An efficient, palladium-catalyzed, enantioselective synthesis of (2R)-3-butene-1,2-diol and its use in highly selective Heck reactions

被引：24

作者：

Cheeseman, N ^{[1
]}

Fox, M ^{[1
]}

Jackson, M ^{[1
]}

Lennon, IC ^{[1
]}

Meek, G ^{[1
]}

机构：

[1] Chirotech Technol Ltd, Dowpharma, Cambridge CB4 0WG, England

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2004年 / 101卷 / 15期

关键词：

D O I：

10.1073/pnas.0307047101

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

A robust and scalable procedure for the palladium-catalyzed dynamic kinetic asymmetric transformation of 3,4-epoxy-1-butene into (2R)-3-butene-1,2-diol with water as the cosolvent is reported. Examination of the effects of solvent and temperature led to the identification of conditions that permitted use of 0.025 mol % catalyst, providing (2R)-3-butene-1,2-diol in 84% isolated yield and 85% enantiomeric excess. Subsequent Heck reactions with a diverse range of coupling partners are described and the influence of their electronic nature on maintaining the enantiopurity of the diol is discussed.

引用

页码：5396 / 5399

页数：4

共 21 条

[1] AMINE ASSISTED ENZYMATIC ESTERIFICATION OF 1,2-DIOL MONOTOSYLATES [J].

BOAZ, NW ;

ZIMMERMAN, RL .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :153-156

[2] Kinetic chiral resolutions of 1,2-diols and desymmetrization of glycerol catalyzed by glycerol kinase [J].

Chenault, HK ;

Chafin, LF ;

Liehr, S .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :4039-4045

[3] AN EXPEDIENT APPROACH TO (2R,3S)-3-AZIDO-1,2-EPOXY-4-PHENYL BUTANE - A KEY INTERMEDIATE FOR HIV PROTEASE INHIBITORS [J].

GURJAR, MK ;

DEVI, NR .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :755-758

[4] PALLADIUM-CATALYZED ARYLATION OF ALLYLIC ALCOHOLS - HIGHLY SELECTIVE SYNTHESIS OF BETA-AROMATIC CARBONYL-COMPOUNDS OR BETA-AROMATIC ALPHA,BETA-UNSATURATED ALCOHOLS [J].

JEFFERY, T .

TETRAHEDRON LETTERS, 1991, 32 (19) :2121-2124

[5] (R)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE AND (S)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE IN STEREOSELECTIVE ORGANIC-SYNTHESIS [J].

JURCZAK, J ;

PIKUL, S ;

BAUER, T .

TETRAHEDRON, 1986, 42 (02) :447-488

[6] PALLADIUM-CATALYZED ARYLATION OF ALLYLIC DIOLS - HIGHLY SELECTIVE SYNTHESIS OF PHENYL-SUBSTITUTED ALLYLIC DIOLS [J].

KANG, SK ;

JUNG, KY ;

PARK, CH ;

NAMKOONG, EY ;

KIM, TH .

TETRAHEDRON LETTERS, 1995, 36 (35) :6287-6290

[7]

MANDAI T, 1990, SYNLETT, P85

[8] Palladium-catalyzed coupling reactions of bromobenzaldehydes with 3,4-di(tert-butyldimethylsilyloxy)-1-alkene to (3,4-dihydroxyalkenyl)benzaldehydes in the synthesis of lipoxin analogues [J].

Nokami, J ;

Furukawa, A ;

Okuda, Y ;

Hazato, A ;

Kurozumi, S .

TETRAHEDRON LETTERS, 1998, 39 (09) :1005-1008

[9] AN ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE (S)-(+)-LINALOOL (3,7-DIMETHYL-1,6-OCTADIEN-3-OL) AND A FORMAL SYNTHESIS OF (R)-(-)-LINALOOL [J].

OHWA, M ;

KOGURE, T ;

ELIEL, EL .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (13) :2599-2601

[10] PALLADIUM-CATALYZED ARYLATION OF N-ALKYL O-ALLYL CARBAMATES - SYNTHESIS OF CINNAMYL ALCOHOLS VIA HECK ARYLATION [J].

ONO, K ;

FUGAMI, K ;

TANAKA, S ;

TAMARU, Y .

TETRAHEDRON LETTERS, 1994, 35 (24) :4133-4136

← 1 2 3 →