Dynamic kinetic resolution of atropisomeric amides

Vincent Chan; Jeung Gon Kim; Ciril Jimeno; Patrick J. Carroll; Patrick J. Walsh

doi:10.1021/ol0492952

Dynamic kinetic resolution of atropisomeric amides

Vincent Chan
, Jeung Gon Kim
, Ciril Jimeno
, Patrick J. Carroll
, Patrick J. Walsh

Biomedical Engineering & Biotechnology

University of Pennsylvania

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

80 Scopus citations

Abstract

Equation presented. Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82% to 95% and the diastereoselectivities from 2.1:1 to 7.0:1.

Original language	British English
Pages (from-to)	2051-2053
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	12
DOIs	https://doi.org/10.1021/ol0492952
State	Published - 10 Jun 2004

Access to Document

10.1021/ol0492952

Cite this

@article{566a0020923244c4a6af11bd1b7d50a7,

title = "Dynamic kinetic resolution of atropisomeric amides",

abstract = "Equation presented. Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82\% to 95\% and the diastereoselectivities from 2.1:1 to 7.0:1.",

author = "Vincent Chan and Kim, \{Jeung Gon\} and Ciril Jimeno and Carroll, \{Patrick J.\} and Walsh, \{Patrick J.\}",

year = "2004",

month = jun,

day = "10",

doi = "10.1021/ol0492952",

language = "British English",

volume = "6",

pages = "2051--2053",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Dynamic kinetic resolution of atropisomeric amides

AU - Chan, Vincent

AU - Kim, Jeung Gon

AU - Jimeno, Ciril

AU - Carroll, Patrick J.

AU - Walsh, Patrick J.

PY - 2004/6/10

Y1 - 2004/6/10

N2 - Equation presented. Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82% to 95% and the diastereoselectivities from 2.1:1 to 7.0:1.

AB - Equation presented. Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82% to 95% and the diastereoselectivities from 2.1:1 to 7.0:1.

UR - https://www.scopus.com/pages/publications/3042809540

U2 - 10.1021/ol0492952

DO - 10.1021/ol0492952

M3 - Article

C2 - 15176816

AN - SCOPUS:3042809540

SN - 1523-7060

VL - 6

SP - 2051

EP - 2053

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Dynamic kinetic resolution of atropisomeric amides

Abstract

Access to Document

Other files and links

Fingerprint

Cite this