Complementary stereochemical outcomes in proline-based self-regenerations of stereocenters

Brian J. Knight; Erin E. Stache; Eric M. Ferreira

doi:10.1021/ol403320d

Complementary stereochemical outcomes in proline-based self-regenerations of stereocenters

Brian J. Knight, Erin E. Stache, Eric M. Ferreira

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

14 Scopus citations

Abstract

Stereoselective alkylations of proline-based amino amides are described, where high levels of either a cis or trans configuration can be attained simply by the choice of the aminal group. Isobutryaldehyde-derived aminals provide the cis configuration, while 1-naphthaldehyde-derived aminals engender the complementary trans configuration.

Original language	English (US)
Pages (from-to)	432-435
Number of pages	4
Journal	Organic letters
Volume	16
Issue number	2
DOIs	https://doi.org/10.1021/ol403320d
State	Published - Jan 17 2014
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol403320d

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title = "Complementary stereochemical outcomes in proline-based self-regenerations of stereocenters",

abstract = "Stereoselective alkylations of proline-based amino amides are described, where high levels of either a cis or trans configuration can be attained simply by the choice of the aminal group. Isobutryaldehyde-derived aminals provide the cis configuration, while 1-naphthaldehyde-derived aminals engender the complementary trans configuration.",

author = "Knight, {Brian J.} and Stache, {Erin E.} and Ferreira, {Eric M.}",

year = "2014",

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AU - Knight, Brian J.

AU - Stache, Erin E.

AU - Ferreira, Eric M.

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Y1 - 2014/1/17

N2 - Stereoselective alkylations of proline-based amino amides are described, where high levels of either a cis or trans configuration can be attained simply by the choice of the aminal group. Isobutryaldehyde-derived aminals provide the cis configuration, while 1-naphthaldehyde-derived aminals engender the complementary trans configuration.

AB - Stereoselective alkylations of proline-based amino amides are described, where high levels of either a cis or trans configuration can be attained simply by the choice of the aminal group. Isobutryaldehyde-derived aminals provide the cis configuration, while 1-naphthaldehyde-derived aminals engender the complementary trans configuration.

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Complementary stereochemical outcomes in proline-based self-regenerations of stereocenters

Abstract

All Science Journal Classification (ASJC) codes

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