Azaenolates of 2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline - A highly diastereo- and enantioselective synthesis of oxazolinyloxiranes

被引:0
作者
Capriati, V [1 ]
Florio, S [1 ]
Luisi, R [1 ]
机构
[1] Univ Bari, Dipartimento Farmacochim, Ctr CNR MISO, I-70125 Bari, Italy
关键词
heterocycles; titanium; asymmetric synthesis; nitrogen heterocycles;
D O I
10.1002/1099-0690(200106)2001:11<2035::AID-EJOC2035>3.0.CO;2-R
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxazoline-derived titanium azaenolate 6 couples highly stereoselectively with aldehydes affording highly optically pure oxazolinyloxiranes 7. The epoxide 7a has been deblocked to form the optically pure formyl oxirane 9. In contrast, the corresponding boron azaenolates 2 and 3 couple with very poor or no stereoselectivity. Lithium, aluminum and tin azaenolates have also been shortly studied.
引用
收藏
页码:2035 / 2039
页数:5
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