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Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark,...
Transcript of Stereocontrolled Domino Reactions · condition, addition of reagents or coupling partners (Denmark,...
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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
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).
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
4 Anionic Primary Step: Domino Michael/Dieckmann Reaction
Groth, U.; Kesenheimer, C.; Kreye, P. Synlett 2006, 2223–2226.
(–)-chokol A
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.
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.
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.
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.
Cationic Sequences: Oxidative Domino Prins/Pinacol Reaction
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Beaulieu, M.-A.; Guérard, K. C.; Maertens, G.; Sabot, C.; Canesi, S. J. Org. Chem. 2011, 76, 9460–9471.
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.
11 Question 2: Mechanism
Lavigne, R. M. A.; Riou, M.; Girardin, M.; Morency, L.; Barriault, L. Org. Lett., 2005, 7, 5921–5923.
Domino Prins/Pinacol Reaction 12
Lavigne, R. M. A.; Riou, M.; Girardin, M.; Morency, L.; Barriault, L. Org. Lett., 2005, 7, 5921–5923.
13 Domino Prins/Pinacol Reaction: Mechanism
Lavigne, R. M. A.; Riou, M.; Girardin, M.; Morency, L.; Barriault, L. Org. Lett., 2005, 7, 5921–5923.
Domino Reactions Initiated by a Pericyclic Primary Step: Domino Alkylation, Oxy-Cope, Cyclization
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Chen, C.; Layton, M. E.; Sheehan, S. M.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 7424–7425.
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
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.
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.
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.
19 Question 4: Product and Mechanism
Muroni, D.; Mucedda, M.; Saba, A. Tetrahedron: Asymmetry 2009, 20, 1154–1159.
20 Question 4: Product and Mechanism
Muroni, D.; Mucedda, M.; Saba, A. Tetrahedron: Asymmetry 2009, 20, 1154–1159.
Transition-metal-catalyzed Domino Reactions: Domino Metathesis Reaction
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Schubert, M.; Metz, P. Angew. Chem., Int. Ed. 2011, 50, 2954–2956.
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Gibbs, R. A.; Okamura, W. H. J. Am. Chem. Soc. 1988, 110, 4062–4063.
Domino [2,3] Rearrangement, Diels-Alder Reaction
Question 5: Mechanism 23
Iglesias, B.; Torrado, A.; de Lera, A. R. J. Org. Chem. 2000, 65, 2696–2705.
Question 5: Mechanism 24
Iglesias, B.; Torrado, A.; de Lera, A. R. J. Org. Chem. 2000, 65, 2696–2705.
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.
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.