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

15 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

Cite this

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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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doi = "10.1021/ol403320d",

language = "English (US)",

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journal = "Organic letters",

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AU - Knight, Brian J.

AU - Stache, Erin E.

AU - Ferreira, Eric M.

PY - 2014/1/17

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.

UR - https://www.scopus.com/pages/publications/84896760465

UR - https://www.scopus.com/pages/publications/84896760465#tab=citedBy

U2 - 10.1021/ol403320d

DO - 10.1021/ol403320d

M3 - Article

C2 - 24377839

AN - SCOPUS:84896760465

SN - 1523-7060

VL - 16

SP - 432

EP - 435

JO - Organic letters

JF - Organic letters

IS - 2

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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