Synthesis of Eight‐Membered Lactams through Formal [6+2] Cyclization of Siloxy Alkynes and Vinylazetidines | Zendy

Wu An | Zendy; Feng Qiang | Zendy; Sung Herman H. Y. | Zendy; Williams Ian D. | Zendy; Sun Jianwei | Zendy

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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.

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