Highly Enantioselective and Efficient Organocatalytic Aldol Reaction of Acetone and β,γ-Unsaturated α-Keto Ester

Pengfei Li; Junling Zhao; Fengbo Li; Albert S.C. Chan; Fuk Yee Kwong

doi:10.1021/ol102254q

Highly Enantioselective and Efficient Organocatalytic Aldol Reaction of Acetone and β,γ-Unsaturated α-Keto Ester

Pengfei Li, Junling Zhao, Fengbo Li, Albert S.C. Chan^*, Fuk Yee Kwong^*

^*Corresponding author for this work

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Abstract

An effective organocatalytic asymmetric aldol reaction of acetone to β,-unsaturated -keto ester has been developed. In the presence of 5 mol % of 9-amino (9-deoxy)-epicinchona alkaloid and 10 mol % of 4-nitrobenzoic acid, the aldol adducts containing a chiral tertiary alcohol moiety were obtained in excellent yields and enantioselectivities.

Original language	English
Pages (from-to)	5616-5619
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	24
Early online date	11 Nov 2010
DOIs	https://doi.org/10.1021/ol102254q
Publication status	Published - 17 Dec 2010

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10.1021/ol102254q

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@article{77de93bec85645ee9c3ccda71c4659cc,

title = "Highly Enantioselective and Efficient Organocatalytic Aldol Reaction of Acetone and β,γ-Unsaturated α-Keto Ester",

abstract = "An effective organocatalytic asymmetric aldol reaction of acetone to β,-unsaturated -keto ester has been developed. In the presence of 5 mol % of 9-amino (9-deoxy)-epicinchona alkaloid and 10 mol % of 4-nitrobenzoic acid, the aldol adducts containing a chiral tertiary alcohol moiety were obtained in excellent yields and enantioselectivities.",

author = "Pengfei Li and Junling Zhao and Fengbo Li and Chan, {Albert S.C.} and Kwong, {Fuk Yee}",

note = "We thank the European Commision FP7-201431 (CATAFLU.OR) and PolyU Internal Grant DA (A-PD0X) for financial support. Prof. Zhongyuan Zhou is gratefully acknowledged for X-ray crystal structure determination. Publisher copyright: {\textcopyright} 2010 American Chemical Society",

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day = "17",

doi = "10.1021/ol102254q",

language = "English",

volume = "12",

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journal = "Organic Letters",

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TY - JOUR

T1 - Highly Enantioselective and Efficient Organocatalytic Aldol Reaction of Acetone and β,γ-Unsaturated α-Keto Ester

AU - Li, Pengfei

AU - Zhao, Junling

AU - Li, Fengbo

AU - Chan, Albert S.C.

AU - Kwong, Fuk Yee

N1 - We thank the European Commision FP7-201431 (CATAFLU.OR) and PolyU Internal Grant DA (A-PD0X) for financial support. Prof. Zhongyuan Zhou is gratefully acknowledged for X-ray crystal structure determination. Publisher copyright: © 2010 American Chemical Society

PY - 2010/12/17

Y1 - 2010/12/17

N2 - An effective organocatalytic asymmetric aldol reaction of acetone to β,-unsaturated -keto ester has been developed. In the presence of 5 mol % of 9-amino (9-deoxy)-epicinchona alkaloid and 10 mol % of 4-nitrobenzoic acid, the aldol adducts containing a chiral tertiary alcohol moiety were obtained in excellent yields and enantioselectivities.

AB - An effective organocatalytic asymmetric aldol reaction of acetone to β,-unsaturated -keto ester has been developed. In the presence of 5 mol % of 9-amino (9-deoxy)-epicinchona alkaloid and 10 mol % of 4-nitrobenzoic acid, the aldol adducts containing a chiral tertiary alcohol moiety were obtained in excellent yields and enantioselectivities.

UR - http://www.scopus.com/inward/record.url?scp=78650318004&partnerID=8YFLogxK

U2 - 10.1021/ol102254q

DO - 10.1021/ol102254q

M3 - Journal article

AN - SCOPUS:78650318004

SN - 1523-7060

VL - 12

SP - 5616

EP - 5619

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Highly Enantioselective and Efficient Organocatalytic Aldol Reaction of Acetone and β,γ-Unsaturated α-Keto Ester

Abstract

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