Highly efficient organocatalytic kinetic resolution of activated nitroallylic acetates with aldehydes via conjugate addition-elimination

Raju Jannapu Reddy; Kwunmin Chen

doi:10.1021/ol200133y

Highly efficient organocatalytic kinetic resolution of activated nitroallylic acetates with aldehydes via conjugate addition-elimination

Raju Jannapu Reddy, Kwunmin Chen^*

^*Corresponding author for this work

Department of Chemistry

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

50 Citations (Scopus)

Abstract

A novel, efficient, and unprecedented organocatalytic kinetic resolution has been developed. For the first time, a variety of nitroallylic acetates 1a-i have been resolved with aldehydes in the presence of 2 (2.5 mol %) via conjugate addition-elimination. The densely functionalized products 3a-o were obtained with excellent enantioselectivities (up to >99% ee), and unreacted substrates 1a-i were recovered with good to excellent optical purity (up to 98% ee).

Original language	English
Pages (from-to)	1458-1461
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	6
DOIs	https://doi.org/10.1021/ol200133y
Publication status	Published - 2011 Mar 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A novel, efficient, and unprecedented organocatalytic kinetic resolution has been developed. For the first time, a variety of nitroallylic acetates 1a-i have been resolved with aldehydes in the presence of 2 (2.5 mol %) via conjugate addition-elimination. The densely functionalized products 3a-o were obtained with excellent enantioselectivities (up to >99% ee), and unreacted substrates 1a-i were recovered with good to excellent optical purity (up to 98% ee).",

author = "Reddy, {Raju Jannapu} and Kwunmin Chen",

year = "2011",

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doi = "10.1021/ol200133y",

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AU - Chen, Kwunmin

PY - 2011/3/18

Y1 - 2011/3/18

N2 - A novel, efficient, and unprecedented organocatalytic kinetic resolution has been developed. For the first time, a variety of nitroallylic acetates 1a-i have been resolved with aldehydes in the presence of 2 (2.5 mol %) via conjugate addition-elimination. The densely functionalized products 3a-o were obtained with excellent enantioselectivities (up to >99% ee), and unreacted substrates 1a-i were recovered with good to excellent optical purity (up to 98% ee).

AB - A novel, efficient, and unprecedented organocatalytic kinetic resolution has been developed. For the first time, a variety of nitroallylic acetates 1a-i have been resolved with aldehydes in the presence of 2 (2.5 mol %) via conjugate addition-elimination. The densely functionalized products 3a-o were obtained with excellent enantioselectivities (up to >99% ee), and unreacted substrates 1a-i were recovered with good to excellent optical purity (up to 98% ee).

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Highly efficient organocatalytic kinetic resolution of activated nitroallylic acetates with aldehydes via conjugate addition-elimination

Abstract

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