Stereochemically controlled synthesis of 1,8-dioxaspiro[4.5]decanes and 1-oxa-8-thiaspiro[4.5]decanes by phenylsulfanyl migration

被引：10

作者：

Eames, J

Heras, MAD

Jones, RVH

Warren, S

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

[2] ZENECA,PROCESS TECHNOL PROGRAM,GRANGEMOUTH WORKS,GRANGEMOUTH FK3 8XG,SCOTLAND

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 26期

关键词：

D O I：

10.1016/0040-4039(96)00851-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Single enantiomers and diastereoisomers of 2- and 3-alkyl-4-phenylsulfanyl-1,8-dioxa- and 1-oxa-8-thiaspiro[4.5]decanes can be prepared in good yield by acid-catalysed phenylsulfanyl migration. Either syn or anti stereochemistry can be selected by aldol reactions or by reduction of hydroxy-ketones. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：4581 / 4584

页数：4

相关论文

共 25 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]

ARENTZEN R, 1975, SYNTHESIS-STUTTGART, P509

[3] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].

CHEN, KM ;

HARDTMANN, GE ;

PRASAD, K ;

REPIC, O ;

SHAPIRO, MJ .

TETRAHEDRON LETTERS, 1987, 28 (02) :155-158

[4]

CHHIBALE K, 1995, J CHEM SOC P1, P2411

[5] 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

[6] ACYCLIC STEREOSELECTION .48. REVERSAL OF STEREOCHEMISTRY IN THE ALDOL REACTIONS OF A CHIRAL BORON ENOLATE [J].

DANDA, H ;

HANSEN, MM ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :173-181

[7]

DEGROOT A, 1985, SYNTHESIS-STUTTGART, P434

[8] A NOVEL SYNTHESIS OF ALPHA-SULFENYLATED ALDEHYDES [J].

DEGROOT, A ;

JANSEN, BJM .

TETRAHEDRON LETTERS, 1981, 22 (09) :887-888

[9] Scope and limitation of the [1,4] SPh shift in the synthesis of allylic alcohols [J].

Eames, J ;

delasHeras, MA ;

Jones, RVH ;

Warren, S .

TETRAHEDRON LETTERS, 1996, 37 (07) :1117-1120

[10] SULFUR PARTICIPATION IN SOLVOLYSIS INVOLVING 4-MEMBERED RING INTERMEDIATES [J].

ELIEL, EL ;

PEARSON, WH ;

JEWELL, LM ;

ABATJOGLOU, AC .

TETRAHEDRON LETTERS, 1980, 21 (04) :331-334