Studies on mercury(II)-mediated opening of bi- and tercyclopropane arrays

被引：27

作者：

Barrett, AGM

Tam, W

机构：

[1] Department of Chemistry, Imperial College of Science, Technology and Medicine, London

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 14期

关键词：

D O I：

10.1021/jo970464o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first examples of the mercury(II)-mediated ring opening of bicyclopropane and tercyclopropane arrays have been investigated. The presence of an adjacent cyclopropyl group dramatically increased the rate of the mercury-mediated opening of the first cyclopropane in a cyclopropane array. In contrast to the mercury-mediated ring opening of monocyclopropanes which usually undergo a concerted ring-opening mechanism, electrophilic openings of cyclopropane arrays occurred through a stabilized, free carbocation. Excellent regio- and stereoselectivities were observed in the mercury-mediated intramolecular openings of the second cyclopropanes in the cyclopropane arrays, giving rise to the formation of enantiomerically pure, highly substituted tetrahydrofurans.

引用

页码：4653 / 4664

页数：12

共 47 条

[1] [1,4] AND [5,5] THERMAL SIGMATROPIC REARRANGEMENTS OF 2-PENTADIENYLOXYPYRIDINE N-OXIDES
ALKER, D
OLLIS, WD
SHAHRIARIZAVAREH, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06): : 1637 - 1643
[2] BACKVALL JE, 1985, J AM CHEM SOC, V107, P7408
[3] Total synthesis and stereochemical assignment of the quinquecyclopropane-containing cholesteryl ester transfer protein inhibitor U-106305
Barrett, AGM
Hamprecht, D
White, AJP
Williams, DJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (33) : 7863 - 7864
[4] Total synthesis of the pentacyclopropane antifungal agent FR-900848
Barrett, AGM
Kasdorf, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) : 11030 - 11037
[5] APPROACHES TO THE ASSEMBLY OF THE ANTIFUNGAL AGENT FR-900848 - STUDIES ON DOUBLE ASYMMETRIC CYCLOPROPANATION AND AN X-RAY CRYSTALLOGRAPHIC STUDY OF (1R,2R)-1,2-BIS-[(1S,2S)-2-METHYLCYCLOPROPYL]-1,2-ETHANEDIYL 3,5-DINITROBENZOATE
BARRETT, AGM
KASDORF, K
WILLIAMS, DJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (15) : 1781 - 1782
[6] Asymmetric synthesis of bicyclopropane derivatives
Barrett, AGM
Doubleday, WW
Tustin, GJ
[J]. TETRAHEDRON, 1996, 52 (48) : 15325 - 15338
[7] STUDIES TOWARDS THE SYNTHESIS OF FR-900848 - STEREOSELECTIVE PREPARATION OF ANTI-BICYCLOPROPANE DERIVATIVES
BARRETT, AGM
TUSTIN, GJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (03) : 355 - 356
[8] APPROACHES TO THE ASSEMBLY OF THE ANTIFUNGAL AGENT FR-900848 - STUDIES ON THE SYNTHESIS OF C-2 SYMMETRICAL TETRACYCLOPROPANE DERIVATIVES AND AN X-RAY CRYSTALLOGRAPHIC STUDY OF (1R,3S,4S,6R)-BICYCLOPROPYL-1,6-DI-(2-[(4R,5R)-DI(ISOPROPYLOXYCARBONYL)-1,3-DIOXOLANE])
BARRETT, AGM
DOUBLEDAY, WW
KASDORF, K
TUSTIN, GJ
WHITE, AJP
WILLIAMS, DJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (04) : 407 - 408
[9] APPROACHES TO THE ASSEMBLY OF THE ANTIFUNGAL AGENT FR-900848 - DETERMINATION OF THE GEOMETRY OF THE DICYCLOPROPYLETHENE UNIT AND AN X-RAY CRYSTALLOGRAPHIC STUDY OF (1R,2S)-1,2-BIS[(1S,2S)-2-METHYLCYCLOPROPYL]-1,2-ETHANEDIYL 3,5-DINITROBENZOATE
BARRETT, AGM
KASDORF, K
WHITE, AJP
WILLIAMS, DJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (06) : 649 - 650
[10] BARRETT AGM, 1996, J CHEM SOC CHEM COMM, P325

← 1 2 3 4 5 →