Enantioselective cycloadditions with α,β-disubstituted acrylimides

Mukund P. Sibi; Zhihua Ma; Kennosuke Itoh; Narayanasamy Prabagaran; Craig P. Jasperse

doi:10.1021/ol050599d

Enantioselective cycloadditions with α,β-disubstituted acrylimides

Mukund P. Sibi, Zhihua Ma, Kennosuke Itoh, Narayanasamy Prabagaran, Craig P. Jasperse

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

63 Scopus citations

Abstract

(Chemical Equation Presented) The use of N-H imide templates provides a solution to the problem of rotamer control in Lewis acid catalyzed reactions of α,β-disubstituted acryloyl imides. Reactions proceed through the s-cis rotamer and with improved reactivity because A^1,3 strain is avoided. Enantioselective nitrone, nitrile oxide, and Diels-Alder cycloadditions demonstrate the principle.

Original language	English (US)
Pages (from-to)	2349-2352
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	12
DOIs	https://doi.org/10.1021/ol050599d
State	Published - Jun 9 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Chemical Equation Presented) The use of N-H imide templates provides a solution to the problem of rotamer control in Lewis acid catalyzed reactions of α,β-disubstituted acryloyl imides. Reactions proceed through the s-cis rotamer and with improved reactivity because A1,3 strain is avoided. Enantioselective nitrone, nitrile oxide, and Diels-Alder cycloadditions demonstrate the principle.",

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T1 - Enantioselective cycloadditions with α,β-disubstituted acrylimides

AU - Sibi, Mukund P.

AU - Ma, Zhihua

AU - Itoh, Kennosuke

AU - Prabagaran, Narayanasamy

AU - Jasperse, Craig P.

PY - 2005/6/9

Y1 - 2005/6/9

N2 - (Chemical Equation Presented) The use of N-H imide templates provides a solution to the problem of rotamer control in Lewis acid catalyzed reactions of α,β-disubstituted acryloyl imides. Reactions proceed through the s-cis rotamer and with improved reactivity because A1,3 strain is avoided. Enantioselective nitrone, nitrile oxide, and Diels-Alder cycloadditions demonstrate the principle.

AB - (Chemical Equation Presented) The use of N-H imide templates provides a solution to the problem of rotamer control in Lewis acid catalyzed reactions of α,β-disubstituted acryloyl imides. Reactions proceed through the s-cis rotamer and with improved reactivity because A1,3 strain is avoided. Enantioselective nitrone, nitrile oxide, and Diels-Alder cycloadditions demonstrate the principle.

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ER -

Enantioselective cycloadditions with α,β-disubstituted acrylimides

Abstract

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