ENANTIOSELECTIVE PREPARATION OF BETA-ALKYL-GAMMA-BUTYROLACTONES FROM FUNCTIONALIZED KETENE DITHIOACETALS

被引：130

作者：

KOCH, SSC ^{[1
]}

CHAMBERLIN, AR ^{[1
]}

机构：

[1] UNIV CALIF IRVINE, DEPT CHEM, IRVINE, CA 92717 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 10期

关键词：

D O I：

10.1021/jo00062a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and general enantioselective synthesis of beta-alkyl-gamma-butyrolactones has been developed. The key step of this procedure is an oxazolidinone-directed alkylation of a lithiated ketene dithioacetal that proceeds with excellent regiochemical control and high diastereofacial selectivity. Reductive removal of the chiral auxiliary followed by acid-induced cyclization of the resultant hydroxy ketene dithioacetal gives the enantiomerically pure beta-alkyl-gamma-butyrolactone.

引用

页码：2725 / 2737

页数：13

共 217 条

[1] ACHIWA K, 1987, TETRAHEDRON LETT, P3675
[2] ACHIWA K, 1986, TETRAHEDRON LETT, P4477
[3] AHLBRECHT H, 1977, CHIMIA, V31, P391
[4] SYNTHESIS OF BOTH ENANTIOMERS OF OPTICALLY PURE SATURATED AND ALPHA,BETA-UNSATURATED GAMMA-SUBSTITUTED GAMMA-LACTONES FROM CHIRAL SULFOXIDES - X-RAY MOLECULAR-STRUCTURE OF (3R,4S)-4-METHYL-4-TERT-BUTYL-3-(PARA-TOLYLTHIO)BUTANOLIDE AND OF (3R,4R)-4-(CYCLOHEX-1-ENYL)-4-METHYL-3-(PARA-TOLYLTHIO)BUTANOLIDEL
ALBINATI, A
BRAVO, P
GANAZZOLI, F
RESNATI, G
VIANI, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08): : 1405 - 1415
[5] STEREOSELECTIVE, CATALYTIC REDUCTION OF L-ASCORBIC-ACID - A CONVENIENT SYNTHESIS OF L-GULONO-1,4-LACTONE
ANDREWS, GC
CRAWFORD, TC
BACON, BE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (14) : 2976 - 2977
[6] ENANTIOSELECTIVE SYNTHESIS OF (-)-BOSCHNIALACTONE
ARAI, Y
KAWANAMI, S
KOIZUMI, T
[J]. CHEMISTRY LETTERS, 1990, (09) : 1585 - 1586
[7] AN EFFICIENT AND CONCISE ENTRY TO (-)-4,5-DIHYDROXY-D-THREO-L-NORVALINE - FORMAL SYNTHESIS OF CLAVALANINE
ARIZA, J
FONT, J
ORTUNO, RM
[J]. TETRAHEDRON LETTERS, 1991, 32 (17) : 1979 - 1982
[8] AZERAD R, 1987, TETRAHEDRON LETT, P1109
[9] SYNTHESIS OF SOME NOVEL TRIFLUOROMETHANESULFONATES AND THEIR REACTIONS WITH ALCOHOLS
BEARD, CD
BAUM, K
GRAKAUSK.V
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (21) : 3673 - 3677
[10] FORMATION OF LACTONES VIA A RADICAL RING-CLOSURE MECHANISM
BECKWITH, ALJ
PIGOU, PE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (01) : 85 - 86

← 1 2 3 4 5 6 7 8 9 10 →