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RCM Approach to Complex Polycyclic α‐Hydroxy γ‐Lactams: Synthesis of Indolizinones and Pyrroloazepinones
Author(s) -
GómezSanJuan Asier,
Sotomayor Nuria,
Lete Esther
Publication year - 2013
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/ejoc.201300889
Subject(s) - chemistry , sequence (biology) , combinatorial chemistry , stereochemistry , lactam , chloride , organic chemistry , biochemistry
The allylmagnesium chloride addition/RCM sequence on N ‐alkenyl‐substituted imides provides a mild access to indolizinone and pyrroloazepinone derivatives with the α‐hydroxy‐γ‐lactam framework. The procedure can be applied to the asymmetric synthesis of this type of derivatives, by employing a 2‐ exo ‐hydroxy‐10‐bornylsulfinyl group as a chiral auxiliary. Further functionality can be introduced at the angular position through an α‐amidoalkylation reaction.