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Synthesis of Eight‐Membered Lactams through Formal [6+2] Cyclization of Siloxy Alkynes and Vinylazetidines
Author(s) -
Wu An,
Feng Qiang,
Sung Herman H. Y.,
Williams Ian D.,
Sun Jianwei
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902866
Subject(s) - ketene , sigmatropic reaction , chirality (physics) , chemistry , stereochemistry , combinatorial chemistry , formal synthesis , medicinal chemistry , physics , chiral symmetry , quantum mechanics , nambu–jona lasinio model , quark
A new approach for the efficient synthesis of eight‐membered lactams through formal [6+2] cyclization of siloxy alkynes and vinylazetidines has been developed. Evidence from a chirality transfer experiment suggests that the reaction proceeds via a [3,3]‐sigmatropic rearrangement from a ketene intermediate. This insight led to the development of alternative conditions and use of acyl chlorides as ketene precursors for the [6+2] reaction with vinylazetidines.