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Azaenolates of 2‐Chloromethyl‐4‐methoxymethyl‐5‐phenyl‐2‐oxazoline − A Highly Diastereo‐ and Enantioselective Synthesis of Oxazolinyloxiranes
Author(s) -
Capriati Vito,
Florio Saverio,
Luisi Renzo
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200106)2001:11<2035::aid-ejoc2035>3.0.co;2-r
Subject(s) - chemistry , enantioselective synthesis , oxazoline , stereoselectivity , epoxide , tin , lithium (medication) , titanium , optically active , organic chemistry , stereochemistry , medicinal chemistry , catalysis , medicine , endocrinology
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.