Enantioselective organo-SOMO cascade cycloadditions: A rapid approach to molecular complexity from simple aldehydes and olefins

Nathan T. Jui; Esther C.Y. Lee; David W.C. MacMillan

doi:10.1021/ja104313x

Enantioselective organo-SOMO cascade cycloadditions: A rapid approach to molecular complexity from simple aldehydes and olefins

Nathan T. Jui, Esther C.Y. Lee, David W.C. MacMillan

Research output: Contribution to journal › Article › peer-review

124 Scopus citations

Abstract

A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.

Original language	English (US)
Pages (from-to)	10015-10017
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	132
Issue number	29
DOIs	https://doi.org/10.1021/ja104313x
State	Published - Jul 28 2010

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.",

author = "Jui, \{Nathan T.\} and Lee, \{Esther C.Y.\} and MacMillan, \{David W.C.\}",

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AU - Jui, Nathan T.

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AU - MacMillan, David W.C.

PY - 2010/7/28

Y1 - 2010/7/28

N2 - A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.

AB - A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.

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Enantioselective organo-SOMO cascade cycloadditions: A rapid approach to molecular complexity from simple aldehydes and olefins

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