(R)-2-PHENYLGLYCINE AS A CHIRAL AUXILIARY IN THE ASYMMETRIC-SYNTHESIS OF 2-AZETIDINONES

被引：18
|
作者：
VANMAANEN, HL
JASTRZEBSKI, JTBH
VERWEIJ, J
KIEBOOM, APG
SPEK, AL
VANKOTEN, G
机构：
[1] UNIV UTRECHT,DEBYE INST,DEPT MET MEDIATED SYNTH,PADUALAAN 8,3584 CH UTRECHT,NETHERLANDS
[2] GIST BROCADES R & D,2600 MA DELFT,NETHERLANDS
[3] UNIV UTRECHT,BIJVOET RES CTR,DEPT CRYSTALLOG,3584 CH UTRECHT,NETHERLANDS
来源：
TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 07期
关键词：
D O I：
10.1016/S0957-4166(00)80336-5
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The chlorozinc enolate of ethyl-[(2,2,5,5-tetramethyl-1-aza-2,5-disila)cyclopentyl]-acetate was reacted with the ZnCl2 complex of N-benzylidene-2-phenylglycine methyl ester in THF at -70-degrees-C. After removal of the protecting silyl moiety (3S, 4S, alphaR)-1-(methoxycarbonyl)(phenyl)methyl-3-amino-4-phenyl-2-azetidinone was obtained in 73% yield with >97% d.e.. By treatment with aqueous ammonia complete epimerization at the alpha-position was accomplished. The (3S, 4S, alphaS) enantiomer was crystallized from THF and the absolute configuration was determined by X-Ray crystallography.
引用
收藏
页码：1441 / 1444
页数：4
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