STEREOSELECTIVE SYNTHESIS OF 2,5-DIALKYL-3-(PHENYLSULFONYL) TETRAHYDROFURANS VIA CYCLIZATION OF Z-SULFONYL-SUBSTITUTED HOMOALLYLIC ALCOHOLS

被引：19

作者：

CRAIG, D ^{[1
]}

IKIN, NJ ^{[1
]}

MATHEWS, N ^{[1
]}

SMITH, AM ^{[1
]}

机构：

[1] WELLCOME RES LABS,BECKENHAM BR3 3BS,KENT,ENGLAND

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 41期

关键词：

D O I：

10.1016/0040-4039(95)01524-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Z-Sulfonyl-substituted homoallylic alcohols 3 underwent highly anti-selective base-mediated 5-endo-trig cyclisation reactions to give 25-dialkyl-3-phenylsulfonyl tetrahydrofurans anti-2. A simple steric model is proposed to account for the high selectivities. Tetrahydrofuran 2g was efficiently and stereoselectively sulfenylated at the 3-position to give 6, which was subjected to an oxidation-syn-elimination sequence to give unsaturated cyclic sulfone 7. Treatment of 6 with Lewis acid in the presence of soft carbon nucleophiles gave the products of rearrangement followed by trapping.

引用

页码：7531 / 7534

页数：4

共 5 条

[1] 5-ENDO-TRIGONAL RING CLOSURES OF UNSATURATED SULFONES
AUVRAY, P
KNOCHEL, P
NORMANT, JF
[J]. TETRAHEDRON LETTERS, 1985, 26 (37) : 4455 - 4458
[2] CHEMISTRY OF THE HERBICIDINS - REACTIVITY OF SILYL ENOL ETHERS DERIVED FROM SIMPLE AND CARBOHYDRATE-BASED TETRAHYDROPYRANS
COX, PJ
GRIFFIN, AM
NEWCOMBE, NJ
LISTER, S
RAMSAY, MVJ
ALKER, D
GALLAGHER, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11): : 1443 - 1447
[3] STEREOSELECTIVE SYNTHESIS OF 3-(PHENYLSULFONYL)-2,5-DISUBSTITUTED TETRAHYDROFURANS VIA 5-ENDO-TRIG RING-CLOSURE REACTIONS
CRAIG, D
SMITH, AM
[J]. TETRAHEDRON LETTERS, 1992, 33 (05) : 695 - 698
[4] STEREOSELECTIVE SYNTHESIS OF Z-VINYLIC AND E-VINYLIC SULFONES
JULIA, M
LAUNAY, M
STACINO, JP
VERPEAUX, JN
[J]. TETRAHEDRON LETTERS, 1982, 23 (24) : 2465 - 2468
[5] SYNTHESIS OF ALLYLIC SULFIDES AND SELENIDES BY LEWIS ACID MEDIATED DISPLACEMENT-REACTIONS OF SULFONES
SIMPKINS, NS
[J]. TETRAHEDRON LETTERS, 1988, 29 (51) : 6787 - 6790

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