A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction

David A. Evans; Daniel Seidel; Magnus Rueping; Hon Wai Lam; Jared T. Shaw; C. Wade Downey

doi:10.1021/ja0373871

A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction

David A. Evans^*, Daniel Seidel, Magnus Rueping, Hon Wai Lam, Jared T. Shaw, C. Wade Downey

^*Corresponding author for this work

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

498 Scopus citations

Abstract

A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.

Original language	English (US)
Pages (from-to)	12692-12693
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	42
DOIs	https://doi.org/10.1021/ja0373871
State	Published - Oct 22 2003
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja0373871

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title = "A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction",

abstract = "A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.",

author = "Evans, {David A.} and Daniel Seidel and Magnus Rueping and Lam, {Hon Wai} and Shaw, {Jared T.} and Downey, {C. Wade}",

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AU - Evans, David A.

AU - Seidel, Daniel

AU - Rueping, Magnus

AU - Lam, Hon Wai

AU - Shaw, Jared T.

AU - Downey, C. Wade

PY - 2003/10/22

Y1 - 2003/10/22

N2 - A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.

AB - A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.

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U2 - 10.1021/ja0373871

DO - 10.1021/ja0373871

M3 - Article

C2 - 14558801

AN - SCOPUS:0142040727

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EP - 12693

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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ER -

A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction

Abstract

ASJC Scopus subject areas

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