STEREOSELECTIVE SYNTHESIS OF CYCLOPROPANONE KETALS VIA SILYL CHLORIDE PROMOTED CYCLIZATION OF BETA-ZINCIOPROPIONATES

被引：9

作者：

YASUI, K ^{[1
]}

TANAKA, S ^{[1
]}

TAMARU, Y ^{[1
]}

机构：

[1] NAGASAKI UNIV, FAC ENGN, DEPT APPL CHEM, NAGASAKI 852, JAPAN

来源：

TETRAHEDRON | 1995年 / 51卷 / 25期

关键词：

D O I：

10.1016/0040-4020(95)00331-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkyl, allyl and propargyl beta-iodopropionates undergo a cyclopropanation by the reaction with zinc-copper couple and TBDMSCI in THF to give 1-alkoxy-, 1-allyloxy-, and 1-propargyloxy-1-tert-butyldimethylsiloxycyclopropanes in moderate or good yields. beta-Iodo-alpha-methylpropionates 2 and 6 provide trans-5 and trans-8 selectively, while beta-iodobutyrates 3 and 7 furnish cis-5 and cis-8 selectively.

引用

页码：6881 / 6900

页数：20

共 27 条

[1]

Davies, Comprehensive Organic Synthesis, 4, (1991)

[2]

Hudlicky, Reed, Comprehensive Organic Synthesis, 5, (1991)

[3]

Charette, Juteau, J. Am. Chem. Soc., 116, (1994)

[4]

Lautens, Delanghe, J. Am. Chem. Soc., 116, (1994)

[5]

Yasui, Fugami, Tanaka, Ii, Yoshida, Tamaru, Tetrahedron Lett., 33, (1992)

[6]

Ruhlman, Die Umsetzung von Carbonsäureestern mit Natrium in Gegenwart von Trimethylchlorsilan, Synthesis, (1971)

[7]

Salaun, Marguerite, CYCLOPROPANONE ETHYL HEMIACETAL FROM ETHYL 3-CHLOROPROPANOATE, Organic Syntheses, 63, (1985)

[8]

Salaun, Cyclopropanone hemiacetals, Chemical Reviews, 83, (1983)

[9]

Kuwajima, Nakamura, Metal homoenolates from siloxycyclopropanes, Topics in Current Chem., 155, (1990)

[10]

Yasui, Fugami, Tanaka, Ii, Yoshida, Saidi, Tamaru, Tetrahedron Lett., 33, (1992)

← 1 2 3 →