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Deprotonation of Oxazolinyloxiranes: Formation of Substituted Acyloxiranes
Author(s) -
Florio Saverio,
Capriati Vito,
Di Martino Serena,
Abbotto Alessandro
Publication year - 1999
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/(sici)1099-0690(199902)1999:2<409::aid-ejoc409>3.0.co;2-z
Subject(s) - chemistry , deprotonation , diastereomer , electrophile , stereochemistry , medicinal chemistry , organic chemistry , catalysis , ion
Deprotonation of oxazolinyloxiranes 1a , 1h , and 1k with s BuLi/TMEDA at –100 °C in Et 2 O furnishes oxazolinyloxiranyllithium compounds [1] 1b , 1i , and 1l which are stable at low temperature and can be trapped with electrophiles to give substituted oxiranes 1c – 1g and 1j . The reaction of 1b with aldehydes produced diastereomers syn ( 2a–d ) and anti ( 3a–d ). Oxiranyllithium 1i from trans ‐1‐(4,4‐dimethyl‐2‐oxazolinyl)‐2‐ p ‐tolylepoxyethane ( 1h ) was found to be configurationally stable while oxiranyllithium 1l , generated from the cis isomer 1k , was not. Oxazolinylepoxides 1d , 1j , and 1m could be deblocked to acyloxiranes 5a – e through oxazolidines 4a – e .