Alkylation of vinyl sulfones as a route to 2-alkylidene tetrahydrofurans

被引：23

作者：

Edwards, GL ^{[1
]}

Sinclair, DJ ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 20期

基金：

澳大利亚研究理事会;

关键词：

sulfones; alkylation; lithiation; regioselection;

D O I：

10.1016/S0040-4039(99)00573-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotonation of the vinyl sulfone (2) with n-butyllithium and treatment of the resulting organolithium intermediate with an alkyl halide in the presence of hexamethylphosphoramide (HMPA) gives monoalkylated adducts in 14 to 61% yields. In general, excellent regioselectivity for alkylation alpha to the sulfone is observed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3933 / 3934

页数：2

共 9 条

[1] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[2] General stereoselective synthesis of (E)-exo-alkylidene tetrahydrofurans via base-mediated cyclization of hydroxyl propargylic sulfones [J].

Dai, WM ;

Lee, MYH .

TETRAHEDRON, 1998, 54 (41) :12497-12512

[3]

Edwards GL, 1997, SYNLETT, P1285

[4] Cyclic enol ether synthesis via arenesulfonyl iodide additions to alkynols [J].

Edwards, GL ;

Muldoon, CA ;

Sinclair, DJ .

TETRAHEDRON, 1996, 52 (22) :7779-7788

[5] GENERATION OF ALPHA-SULFONYLVINYLITHIUM REAGENTS BY THE LITHIATION OF VINYLIC SULFONES [J].

EISCH, JJ ;

GALLE, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (18) :3279-3280

[6]

ELIOT MC, 1997, CONTEMP ORG SYNTH, V4, P238

[7] REACTION BETWEEN 1,1-DILITHIOALKYL PHENYL SULFONES AND OMEGA-BROMOESTERS - SYNTHESIS OF CYCLIC VINYL ETHERS [J].

MUSSATTO, MC ;

SAVOIA, D ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (01) :260-263

[8] 5-MEMBERED AND 6-MEMBERED RING COMPOUNDS FROM (E)-BETA-IODO(VINYL)SULFONES [J].

SHORT, KM ;

ZIEGLER, CB .

TETRAHEDRON LETTERS, 1995, 36 (03) :355-356

[9] Recent advances in annonaceous acetogenins [J].

Zeng, L ;

Ye, Q ;

Oberlies, NH ;

Shi, G ;

Gu, ZM ;

He, K ;

McLaughlin, JL .

NATURAL PRODUCT REPORTS, 1996, 13 (04) :275-306

← 1 →