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1 Stereocontrolled Domino Reactions Pellissier, H. Chem. Rev. 2013, 113, 442–524. Friday Problem Set Qin Zang 2-8-13 Chem. Soc. Rev., 2009, 38, 3092–3101
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Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

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Page 1: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

1

Stereocontrolled Domino Reactions

Pellissier, H. Chem. Rev. 2013, 113, 442–524.

Friday Problem Set

Qin Zang 2-8-13

Chem. Soc. Rev., 2009, 38, 3092–3101

Page 2: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

2 Definition • Descriptors cascade, domino, tandem, and sequential, are used in the

literature, often seemingly interchangeably and with liberal abandon. (Nicolaou, ACIE 2006, 45, 7134).

• A reaction involving two or more bond-forming transformations that take place under the same reaction conditions, without adding additional reagents and catalysts, and in which the subsequent reactions result as a consequence of the functionality formed by bond formation or fragmentation in the previous step (Tietze, ACIE 1993, 32, 131).

• For this type of transformation also the expression cascade has been used; however, this word does not describe the real meaning and is also used in many ways in science for other phenomena.

• Most domino reactions, as defined by Tietze, fell under the broader category of tandem processes. Other tandem reactions that are not cascades involve the isolation of intermediates, a change in reaction condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137).

• Multicomponent reactions should be clearly differentiated from other one-pot processes such as domino, tandem, cascade, or zipper reactions, and in general from all those processes that involve the reaction between two reagents to yield an intermediate which is captured by the successive addition of a new reagent (sequential component reactions (Yus, ACIE 2005, 44, 1602).

Page 3: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

3 Tietze’s Classification

Tietze, L. F. Chem. Rev. 1996, 96, 115–136.

1st step 2nd step 3rd step

cationic cationic cationic

anionic anionic anionic

radical radical radical

pericyclic pericyclic pericyclic

photochemical photochemical photochemical

carbenoid carbenoid carbenoid

transition metal-catalyzed transition metal-catalyzed transition metal-catalyzed

oxidation/reduction oxidation/reduction oxidation/reduction

Page 4: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

4 Anionic Primary Step: Domino Michael/Dieckmann Reaction

Groth, U.; Kesenheimer, C.; Kreye, P. Synlett 2006, 2223–2226.

(–)-chokol A

Page 5: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

5 Question 1: Mechanism

Kinoshita, H.; Osamura, T.; Mizuno, K.; Kinoshita, S.; Iwamura, T.; Watanabe, S.-i.; Kataoka, T.; Muraoka, O.; Tanabe, G. Chem. Eur. J. 2006, 12, 3896–3904.

Page 6: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

6 Proposed Mechanism: Domino Thia-Michael/Aldol Reaction

Kinoshita, H.; Osamura, T.; Mizuno, K.; Kinoshita, S.; Iwamura, T.; Watanabe, S.-i.; Kataoka, T.; Muraoka, O.; Tanabe, G. Chem. Eur. J. 2006, 12, 3896–3904.

Page 7: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Proposed Mechanism: Diastereoselectivity 7

Kinoshita, H.; Osamura, T.; Mizuno, K.; Kinoshita, S.; Iwamura, T.; Watanabe, S.-i.; Kataoka, T.; Muraoka, O.; Tanabe, G. Chem. Eur. J. 2006, 12, 3896–3904.

Page 8: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Proposed Mechanism: Cyclic vs Acyclic Transition State 8

Kinoshita, H.; Osamura, T.; Mizuno, K.; Kinoshita, S.; Iwamura, T.; Watanabe, S.-i.; Kataoka, T.; Muraoka, O.; Tanabe, G. Chem. Eur. J. 2006, 12, 3896–3904.

Page 9: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Cationic Sequences: Oxidative Domino Prins/Pinacol Reaction

9

Beaulieu, M.-A.; Guérard, K. C.; Maertens, G.; Sabot, C.; Canesi, S. J. Org. Chem. 2011, 76, 9460–9471.

Page 10: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Oxidative Domino Prins/Pinacol Reaction 10

Beaulieu, M.-A.; Guérard, K. C.; Maertens, G.; Sabot, C.; Canesi, S. J. Org. Chem. 2011, 76, 9460–9471.

Page 11: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

11 Question 2: Mechanism

Lavigne, R. M. A.; Riou, M.; Girardin, M.; Morency, L.; Barriault, L. Org. Lett., 2005, 7, 5921–5923.

Page 12: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Domino Prins/Pinacol Reaction 12

Lavigne, R. M. A.; Riou, M.; Girardin, M.; Morency, L.; Barriault, L. Org. Lett., 2005, 7, 5921–5923.

Page 13: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

13 Domino Prins/Pinacol Reaction: Mechanism

Lavigne, R. M. A.; Riou, M.; Girardin, M.; Morency, L.; Barriault, L. Org. Lett., 2005, 7, 5921–5923.

Page 14: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Domino Reactions Initiated by a Pericyclic Primary Step: Domino Alkylation, Oxy-Cope, Cyclization

14

Chen, C.; Layton, M. E.; Sheehan, S. M.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 7424–7425.

Page 15: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

15 Domino Fries rearrangement, Cyclization, Deprotection

Chen, C.; Layton, M. E.; Sheehan, S. M.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 7424–7425.

(l) TMSOTf, HC(OMe)3, CH2Cl2,-78 to 0 °C

Page 16: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

16 Question 3: Mechanism

(a) Sauer, E. L. O.; Hooper, J. H.; Woo, T.; Barriault, L. J. Am. Chem. Soc. 2007, 129, 2112–2119. (b) Arns, S.; Barriault, L. Chem. Commun. 2007, 2211–2221.

Page 17: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

17 Question 3: Mechanism

(a) Sauer, E. L. O.; Hooper, J. H.; Woo, T.; Barriault, L. J. Am. Chem. Soc. 2007, 129, 2112–2119. (b) Arns, S.; Barriault, L. Chem. Commun. 2007, 2211–2221.

Page 18: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

18 Carbene Sequences: Domino Carbonyl Ylide Formation /1,3-Dipolar Cycloaddition Reaction

Hirata, Y.; Nakamura, S.; Watanabe, N.; Kataoka, O.; Kurrosaki, Anada, M.; Kitagaki, S.; Shiro, M.; Hashimoto, S. Chem. Eur. J. 2006, 12, 8898–8925.

Page 19: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

19 Question 4: Product and Mechanism

Muroni, D.; Mucedda, M.; Saba, A. Tetrahedron: Asymmetry 2009, 20, 1154–1159.

Page 20: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

20 Question 4: Product and Mechanism

Muroni, D.; Mucedda, M.; Saba, A. Tetrahedron: Asymmetry 2009, 20, 1154–1159.

Page 21: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Transition-metal-catalyzed Domino Reactions: Domino Metathesis Reaction

21

Schubert, M.; Metz, P. Angew. Chem., Int. Ed. 2011, 50, 2954–2956.

Page 22: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

22

Gibbs, R. A.; Okamura, W. H. J. Am. Chem. Soc. 1988, 110, 4062–4063.

Domino [2,3] Rearrangement, Diels-Alder Reaction

Page 23: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Question 5: Mechanism 23

Iglesias, B.; Torrado, A.; de Lera, A. R. J. Org. Chem. 2000, 65, 2696–2705.

Page 24: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Question 5: Mechanism 24

Iglesias, B.; Torrado, A.; de Lera, A. R. J. Org. Chem. 2000, 65, 2696–2705.

Page 25: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

25

Page 26: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Domino Reactions Initiated by an Oxidation 26

Peed, J.; Davies, I. R.; Peacock, L. R.; Taylor, J. E.; Kociok-Köhn, G.; Bull, S. D. J. Org. Chem. 2012, 77, 543–555.

Page 27: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

Domino Reactions Initiated by a Ring-Opening Reaction 27

Fujioka, H.; Matsuda, S.; Horai, M.; Fujii, E.; Morishita, M.; Nishiguchi, N.; Hata, K.; Kita, Y. Chem. Eur. J. 2007, 13, 5238–5248.

Page 28: Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark, Chem. Rev. 1996, 96, 137). • Multicomponent reactions should be clearly differentiated

28 Multicomponent Reactions Domino Michael/Aldol/Retro-Dieckmann Reaction

Coquerel, Y.; Filippini, M.-H.; Bensa, D.; Rodriguez, J. Chem. Eur. J. 2008, 14, 3078.