Cycloaddition of lithium ynolate to imines:: Synthesis of 3,4-disubstituted β-lactams?

被引:22
作者
Shindo, M [1 ]
Oya, S [1 ]
Sato, Y [1 ]
Shishido, K [1 ]
机构
[1] Univ Tokushima, Inst Med Resources, Tokushima 7708505, Japan
关键词
D O I
10.3987/COM-98-S52
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cycloaddition reaction of a lithium ynolate to N-sulfonylimines afforded 3,4-disubstituted beta-lactams. The cis-products were synthesized in high diastereoselectivity via quenching of the intermediate, beta-lactam enolates, with phenol.
引用
收藏
页码:113 / 116
页数:4
相关论文
共 8 条
[1]   NOVEL SYNTHESES OF 3-METHYLENE-AZETIDIN-2-ONE DERIVATIVES AND RELATED SYSTEMS [J].
ADLINGTON, RM ;
BARRETT, AGM ;
QUAYLE, P ;
WALKER, A ;
BETTS, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (09) :404-405
[2]   THE TITANIUM TETRACHLORIDE INDUCED SYNTHESIS OF N-PHOSPHINOYLIMINES AND N-SULPHONYLIMINES DIRECTLY FROM AROMATIC-ALDEHYDES [J].
JENNINGS, WB ;
LOVELY, CJ .
TETRAHEDRON, 1991, 47 (29) :5561-5568
[3]   Ynolates from the reaction of lithiosilyldiazomethane with carbon monoxide. New ketenylation reactions [J].
Kai, H ;
Iwamoto, K ;
Chatani, N ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (32) :7634-7635
[4]   REMOVAL OF TOLUENE-PARA-SULFONYL GROUPS FROM SULFONAMIDES .4. SYNTHESIS OF PHENYLGLYOXAL IMINE MONOMERS [J].
MCKAY, WR ;
PROCTOR, GR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2435-2442
[5]   A synthesis of ynolates via the cleavage of ester dianions [J].
Shindo, M .
TETRAHEDRON LETTERS, 1997, 38 (25) :4433-4436
[6]   Novel synthesis of ynolates via the cleavage of ester dianions:: α-bromo and α,α-dibromo esters as precursors [J].
Shindo, M ;
Sato, Y ;
Shishido, K .
TETRAHEDRON, 1998, 54 (11) :2411-2422
[7]   A highly stereoselective synthesis of tri- and tetrasubstituted olefins via ynolates [J].
Shindo, M ;
Sato, Y ;
Shishido, K .
TETRAHEDRON LETTERS, 1998, 39 (27) :4857-4860
[8]  
SHINDO M, IN PRESS CHEM SOC RE