α-Chiral Acetylenes Having an All-Carbon Quaternary Center: Phase Transfer Catalyzed Enantioselective α Alkylation of α-Alkyl-α-alkynyl Esters

被引：46

作者：

Hashimoto, Takuya ^{[1
]}

Sakata, Kazuki ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 27期

关键词：

alkylation; alkynes; asymmetric synthesis; phase-transfer catalysis; synthetic methods; ASYMMETRIC MANNICH REACTIONS; BETA-SULFONAMIDE ALCOHOL; AMINO-ACID DERIVATIVES; PROPARGYLIC ALCOHOLS; DIRECT-ADDITION; EFFICIENT SYNTHESIS; CONJUGATE ADDITION; TERMINAL ALKYNES; ALDOL REACTION; ALDEHYDES;

D O I：

10.1002/anie.200901977

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Going through the phases: The title reaction was found to proceed by an initial base-mediated isomerization to allenyl esters and subsequent phase transfer catalyzed alkylation at the α position of the ester (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5014 / 5017

页数：4

共 73 条

[11]

Colvin E.W., 1988, SILICON REAGENTS ORG

[12] Enantioselective alkynylation of ketones catalyzed by Zn(salen) complexes [J].

Cozzi, PG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (25) :2895-2898

[13]

COZZI RG, 2004, EUR J ORG CHEM, P4095

[14] Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes [J].

Dhondi, Pawan K. ;

Carberry, Patrick ;

Choi, Lydia B. ;

Chishohm, John D. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9590-9596

[15]

Diederich F, 2005, ACETYLENE CHEMISTRY: CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE, pV

[16] Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes [J].

Frantz, DE ;

Fässler, R ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1806-1807

[17] Aluminum-catalyzed asymmetric alkylations of pyridyl-substituted alkynyl ketones with dialkylzinc reagents [J].

Friel, Donna K. ;

Snapper, Marc L. ;

Hoveyda, Amir H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (30) :9942-9951

[18] Enantioselective, copper(I)-catalyzed three-component reaction for the preparation of propargylamines [J].

Gommermann, N ;

Koradin, X ;

Polborn, K ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5763-5766

[19]

Gommermann N., 2003, Angew. Chem, V115, P5941

[20] Recent development and application of chiral phase-transfer catalysts [J].

Hashimoto, Takuya ;

Maruoka, Keiji .

CHEMICAL REVIEWS, 2007, 107 (12) :5656-5682

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