An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine

被引：30

作者：

Watanabe, Y ^{[1
]}

Mase, N ^{[1
]}

Tateyama, M ^{[1
]}

Toru, T ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(99)00066-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An improved procedure of the Sharpless method for the preparation of chiral sulfinates by triphenylphosphine is described. A mixture of sulfonyl chlorides and diacetone-D-glucose or l-menthol in the presence of triethylamine was treated with triphenylphosphine in CH2Cl2 at 0 degrees C to give the sulfinates in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：737 / 745

页数：9

共 29 条

[21] ASYMMETRIC-SYNTHESIS OF CARBON CARBON BONDS USING SULFINYL CYCLOALKENONES, ALKENOLIDES, AND PYRONES [J].

POSNER, GH .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (02) :72-78

[22] ASYMMETRIC INDUCTION DURING ORGANO-METALLIC CONJUGATE ADDITION TO ENANTIOMERICALLY PURE 2-(ARYLSULFINYL)-2-CYCLOPENTENONES [J].

POSNER, GH ;

MALLAMO, JP ;

HULCE, M ;

FRYE, LL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (15) :4180-4185

[23] A GENERAL-ROUTE TO ENANTIOMERICALLY PURE SULFOXIDES FROM A CHIRAL SULFITE [J].

REBIERE, F ;

SAMUEL, O ;

RICARD, L ;

KAGAN, HB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :5991-5999

[24]

SOLLADIE G, 1981, SYNTHESIS-STUTTGART, P185

[25]

SOLLADIE G, 1987, SYNTHESIS-STUTTGART, P173

[26]

Solladie G., 1991, COMPREHENSIVE ORGANI, V6

[27] ASYMMETRIC CARBON-CARBON BOND FORMATION USING SULFOXIDE-STABILIZED CARBANIONS [J].

WALKER, AJ .

TETRAHEDRON-ASYMMETRY, 1992, 3 (08) :961-998

[28] ASYMMETRIC-SYNTHESIS OF CHIRAL SULFINATE ESTERS AND SULFOXIDES - SYNTHESIS OF SULFORAPHANE [J].

WHITESELL, JK ;

WONG, MS .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :597-601

[29]

WHITMORE FC, 1941, ORG SYNTH, P492

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