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Enantioselective Addition of Iodine Azide to α,β‐Unsaturated Carboxylic Acid Derivatives
Author(s) -
Lee PeyChen,
Wu ChiCheng,
Cheng MingChu,
Wu MingJung
Publication year - 1992
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199200013
Subject(s) - chemistry , regioselectivity , azide , iodine , enantioselective synthesis , conjugated system , organic chemistry , medicinal chemistry , catalysis , polymer
The addition of iodine azide to chiral conjugated N ‐enoyl‐sultam or α,β ‐unsaturated N‐ acyloxazolidinones generated two asymmetric centers at C(α) and C(β) with high π‐face differentiation and regioselectivity. The diastereomerically pure product was easily obtained by crystallization with purity up to 94% de. The structure of 2a was determined by X‐ray diffraction analysis which also indicated that B and 4 are reactive conformations.