Stereochemical control in the synthesis of tetrahydrofurans by cyclisation of diols with [1,2]-phenylsulfanyl migration

被引：13

作者：

Aggarwal, VK

Eames, J

Villa, MJ

McIntyre, S

Sansbury, FH

Warren, S

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

[2] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[3] Queen Mary Univ London, Dept Chem, London E1 4NS, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 04期

关键词：

D O I：

10.1039/a908810e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid catalysed rearrangement of a series of 4-PhS-1,3-diols with toluene-p-sulfonic acid in benzene gives stereospecifically substituted 3-PhS-tetrahydrofurans in excellent yield via a [1,2]-SPh shift. We comment on the structural variation at both the migration origin and terminus on the outcome of the title reaction and define its limits.

引用

收藏

页码：533 / 546

页数：14

相关论文

共 33 条

[1] TRANSFORMATION OF CYCLIC ALPHA-PHENYLTHIO ALDEHYDES BY STEREOSELECTIVE ALDOL REACTIONS AND PHENYLTHIO MIGRATION INTO SPIROCYCLIC LACTONES AND ETHERS, AND E-ALLYLIC ALCOHOLS WITH 1,4-RELATED CHIRAL CENTERS [J].

AGGARWAL, VK ;

COLDHAM, I ;

MCINTYRE, S ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :451-460

[2] STEREOCHEMICAL CONTROL IN THE SYNTHESIS OF TETRAHYDROFURANS BY CYCLIZATION OF DIOLS WITH PHENYLTHIO MIGRATION [J].

AGGARWAL, VK ;

COLDHAM, I ;

MCINTYRE, S ;

SANSBURY, FH ;

VILLA, MJ ;

WARREN, S .

TETRAHEDRON LETTERS, 1988, 29 (38) :4885-4888

[3] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[4]

BESTMANN HJ, 1974, LIEBIGS ANN CHEM, P2085

[5] PHENYLTHIO MIGRATIONS IN REARRANGEMENTS OF 2,2-BISPHENYLTHIOETHANOLS [J].

BLATCHER, P ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (05) :1055-1066

[6] SYNTHESIS OF BUTENOLIDES FROM ALPHA-(PHENYLTHIO)-KETONES AND ALPHA-(PHENYTHIO)-ESTERS - CRYSTAL-STRUCTURE OF AN INTERMEDIATE BETA-PHENYLTHIO-GAMMA-LACTONE [J].

BROWNBRIDGE, P ;

EGERT, E ;

HUNT, PG ;

KENNARD, O ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (10) :2751-2759

[7]

CHEREST M, 1968, TETRAHEDRON LETT, P2199

[8] ASYMMETRIC ALDOL REACTIONS OF ACHIRAL 2-PHENYLSULFANYL ALDEHYDES WITH SMALL-SIZED AND MEDIUM-SIZED CARBOCYCLIC RINGS - THE SYNTHESIS OF HOMOCHIRAL SPIROCYCLIC LACTONES, PYRROLIDINES AND TETRAHYDROFURANS [J].

CHIBALE, K ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (19) :2411-2418

[9] SYNTHESIS OF CYCLIC AMINES AND ALLYLIC SULFIDES BY PHENYLTHIO MIGRATION OF BETA-HYDROXY SULFIDES [J].

COLDHAM, I ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (14) :1637-1656

[10]

DEGROOT A, 1985, SYNTHESIS-STUTTGART, P434

← 1 2 3 4 →