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Base‐Induced Coupling of α‐Azido Ketones with Aldehydes − An Easy and Efficient Route to Trifunctionalized Synthons 2‐Azido‐3‐hydroxy Ketones, 2‐Acylaziridines, and 2‐Acylspiroaziridines
Author(s) -
Patonay Tamás,
JuhászTóth Éva,
Bényei Attila
Publication year - 2002
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(20021)2002:2<285::aid-ejoc285>3.0.co;2-j
Subject(s) - chemistry , synthon , aldol reaction , ketone , coupling (piping) , base (topology) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , mechanical engineering , mathematical analysis , mathematics , engineering
An improved synthesis of α‐azido ketones under phase‐transfer conditions has been developed. The transformation of α‐azido ketones into acyclic and heterocyclic 2‐azido‐3‐hydroxy ketones has been demonstrated and the relative configurations of the chromanone derivatives have been determined by X‐ray analysis. Treatment of the aldol‐type products with triphenylphosphane afforded 2‐acylaziridines and the hitherto unknown spiro[chroman‐3,2′‐aziridin]‐4‐ones. The relative configuration of the spiroaziridines was determined by NOE measurements.