Enantioselective synthesis of α-alkyl-β-ketoesters: Asymmetric Roskamp reaction catalyzed by an oxazaborolidinium ion

Lizhu Gao; Byung Chul Kang; Geum Sook Hwang; Do Hyun Ryu

doi:10.1002/anie.201204350

Enantioselective synthesis of α-alkyl-β-ketoesters: Asymmetric Roskamp reaction catalyzed by an oxazaborolidinium ion

Lizhu Gao, Byung Chul Kang, Geum Sook Hwang, Do Hyun Ryu

Department of Chemistry

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

74 Scopus citations

Abstract

Breaking kamp: A catalytic route toward chiral α-alkyl-β- ketoesters using the title reaction of α-alkyl diazoester with aldehydes has been developed (see scheme). The reaction proceeds with high to excellent enantioselectivities and this methodology was applied to a concise two-step synthesis of the natural pheromone sitophilate.

Original language	English
Pages (from-to)	8322-8325
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	33
DOIs	https://doi.org/10.1002/anie.201204350
State	Published - 13 Aug 2012

Keywords

asymmetric synthesis
boron
diazo compounds
homogeneous catalysis
synthetic methods

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abstract = "Breaking kamp: A catalytic route toward chiral α-alkyl-β- ketoesters using the title reaction of α-alkyl diazoester with aldehydes has been developed (see scheme). The reaction proceeds with high to excellent enantioselectivities and this methodology was applied to a concise two-step synthesis of the natural pheromone sitophilate.",

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author = "Lizhu Gao and Kang, \{Byung Chul\} and Hwang, \{Geum Sook\} and Ryu, \{Do Hyun\}",

year = "2012",

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T1 - Enantioselective synthesis of α-alkyl-β-ketoesters

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AU - Kang, Byung Chul

AU - Hwang, Geum Sook

AU - Ryu, Do Hyun

PY - 2012/8/13

Y1 - 2012/8/13

N2 - Breaking kamp: A catalytic route toward chiral α-alkyl-β- ketoesters using the title reaction of α-alkyl diazoester with aldehydes has been developed (see scheme). The reaction proceeds with high to excellent enantioselectivities and this methodology was applied to a concise two-step synthesis of the natural pheromone sitophilate.

AB - Breaking kamp: A catalytic route toward chiral α-alkyl-β- ketoesters using the title reaction of α-alkyl diazoester with aldehydes has been developed (see scheme). The reaction proceeds with high to excellent enantioselectivities and this methodology was applied to a concise two-step synthesis of the natural pheromone sitophilate.

KW - asymmetric synthesis

KW - boron

KW - diazo compounds

KW - homogeneous catalysis

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/84864879515

U2 - 10.1002/anie.201204350

DO - 10.1002/anie.201204350

M3 - Article

C2 - 22821683

AN - SCOPUS:84864879515

SN - 1433-7851

VL - 51

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EP - 8325

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 33

ER -

Enantioselective synthesis of α-alkyl-β-ketoesters: Asymmetric Roskamp reaction catalyzed by an oxazaborolidinium ion

Abstract

Keywords

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