HIGHLY DIASTEREOSELECTIVE [2+2] CYCLOADDITIONS VIA CHELATION CONTROL - ASYMMETRIC-SYNTHESIS OF BETA-LACTONES

被引:28
作者
ZEMRIBO, R [1 ]
ROMO, D [1 ]
机构
[1] TEXAS A&M UNIV,DEPT CHEM,COLLEGE STN,TX 77843
关键词
D O I
10.1016/0040-4039(95)00716-P
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chelation controlled [2+2] cycloadditions of trimethylsilylketene to chiral alpha- and beta-benzyloxyaldehydes followed by desilylation provides a highly diastereoselective route to functionalized beta-lactones. Several Lewis acids were examined and MgBr2 . Et(2)O was found to give the highest diastereoselectivities and yields.
引用
收藏
页码:4159 / 4162
页数:4
相关论文
共 19 条
[11]  
Black, Zhang, Huang, Syn. Commun., 25, pp. 15-20, (1995)
[12]  
Seebach, Chow, Jackson, Lawson, Sutter, Thaisrivongs, Zimmermann, J. Am. Chem. Soc., 107, pp. 5292-5293, (1985)
[13]  
Takahata, Uchida, Momose, J. Org. Chem., 59, pp. 7201-7208, (1994)
[14]  
Takahata, Uchida, Momose, J. Org. Chem., 59, pp. 7201-7208, (1994)
[15]  
Dale, Dull, Mosher, J. Org. Chem., 34, pp. 2543-2549, (1969)
[16]  
Reetz, Agnew. Chem. Int. Ed. Engl., 23, pp. 556-569, (1984)
[17]  
Danishefsky, Pearson, Harvey, Maring, Springer, J. Am. Chem. Soc., 107, pp. 1256-1268, (1985)
[18]  
Kiyooka, Heathcock, Tetrahedron Lett., 24, pp. 4765-4768, (1983)
[19]  
Keck, Castellino, J. Am. Chem. Soc., 108, pp. 3847-3849, (1986)