Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes

被引：177

作者：

Boyall, D ^{[1
]}

López, F ^{[1
]}

Sasaki, H ^{[1
]}

Frantz, D ^{[1
]}

Carreira, EM ^{[1
]}

机构：

[1] ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 26期

关键词：

D O I：

10.1021/ol006791r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We report the first example of enantioselective aldehyde additions of 2-methyl-3-butyn-2-ol, a commodity bulk chemical that is readily available. Following a facile fragmentation reaction, the addition reactions provide access to optically active terminal acetylenes as useful building blocks for asymmetric synthesis.

引用

页码：4233 / 4236

页数：4

共 18 条

[1] CATALYTIC, ENANTIOSELECTIVE ACETONE ALDOL ADDITIONS WITH 2-METHOXYPROPENE [J].

CARREIRA, EM ;

LEE, W ;

SINGER, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3649-3650

[2] Advances in catalytic, enantioselective aldol addition reactions with novel Ti(IV) complexes [J].

Carreira, EM ;

Singer, RA .

DRUG DISCOVERY TODAY, 1996, 1 (04) :145-150

[3]

CARREIRA EM, UNPUB

[4] HIGHLY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES PROMOTED BY CHIRAL OXAZABOROLIDINES [J].

COREY, EJ ;

CIMPRICH, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3151-3152

[5] Enantiodivergent total syntheses of (+)- and (-)-scopadulcic acid A [J].

Fox, ME ;

Li, C ;

Marino, JP ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5467-5480

[6] 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

[7] The discovery of novel reactivity in the development of C-C bond-forming reactions:: In situ generation of zinc acetylides with ZnII/R3N [J].

Frantz, DE ;

Fässler, R ;

Tomooka, CS ;

Carreira, EM .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :373-381

[8] Catalytic in situ generation of Zn(II)-alkynilides under mild conditions:: A novel C=N addition process utilizing terminal acetylenes [J].

Frantz, DE ;

Fässler, R ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11245-11246

[9] Direct catalytic enantioselective reduction of achiral alpha,beta-ynones. Strong remote steric effects across the C-C triple bond [J].

Helal, CJ ;

Magriotis, PA ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) :10938-10939

[10] Nucleobase recognition by artificial receptors possessing a ferrocene skeleton as a novel modular unit for hydrogen bonding and stacking interactions [J].

Inouye, M ;

Hyodo, Y ;

Nakazumi, H .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2704-2710

← 1 2 →