Practical preparation of N-(1-alkynyl)sulfonamides and their remote diastereoselective addition to aldehydes via titanation

被引：72

作者：

Hirano, S

Tanaka, R

Urabe, H

Sato, F

机构：

[1] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

[2] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Dept Biol Informat, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 05期

关键词：

D O I：

10.1021/ol036396b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aliphatic and aromatic suffonamides were alkynylated with 1-bromo-1-alkynes in the catalytic presence of Cul to give N-(1-alkynyl)sulfonamides in good to excellent yields. The acetylene-titanium complexes generated from N-(1-alkynyl)benzosultams underwent diastereoselective addition to aldehydes.

引用

页码：727 / 729

页数：3

共 30 条

[11] 1,n-dicarbanionic titanium intermediates from monocarbanionic organometallics and their application in organic synthesis [J].

Kulinkovich, OG ;

de Meijere, A .

CHEMICAL REVIEWS, 2000, 100 (08) :2789-2834

[12]

Liu ZP, 2002, HETEROCYCLES, V56, P693

[13] Strategies for the stereoselective synthesis of molecules with remote stereogenic centres across a double bond of fixed configuration [J].

Mitchell, HJ ;

Nelson, A ;

Warren, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (14) :1899-1914

[14]

MURCH P, 1994, SYNTHESIS-STUTTGART, P1255

[15] PATTERNS OF STOICHIOMETRIC AND CATALYTIC REACTIONS OF ORGANOZIRCONIUM AND RELATED COMPLEXES OF SYNTHETIC INTEREST [J].

NEGISHI, E ;

TAKAHASHI, T .

ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (05) :124-130

[16]

NEGISHI EI, 1991, COMPREHENSIVE ORGANI, V5, P1163

[17] CAMPHOR AS A NATURAL SOURCE OF CHIRALITY IN ASYMMETRIC-SYNTHESIS [J].

OPPOLZER, W .

PURE AND APPLIED CHEMISTRY, 1990, 62 (07) :1241-1250

[18] Palladium-catalysed reactions of aryl halides with soft, non-organometallic nucleophiles [J].

Prim, D ;

Campagne, JM ;

Joseph, D ;

Andrioletti, B .

TETRAHEDRON, 2002, 58 (11) :2041-2075

[19] Synthesis of organotitanium complexes from alkenes and alkynes and their synthetic applications [J].

Sato, F ;

Urabe, H ;

Okamoto, S .

CHEMICAL REVIEWS, 2000, 100 (08) :2835-2886

[20]

Sato F, 2002, TITANIUM AND ZIRCONIUM IN ORGANIC SYNTHESIS, P319, DOI 10.1002/3527600671.ch9

← 1 2 3 →