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Direct Synthesis of 6‐Azabicyclo[3.2.1]oct‐6‐en‐2‐ones and Pyrrolizidines from Divinyl Ketones and Observation of Remarkable Substituent Effects
Author(s) -
Xu Xianxiu,
Li Yifei,
Zhang Yu,
Zhang Lingjuan,
Pan Ling,
Liu Qun
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000880
Subject(s) - chemistry , substituent , alkyl , aryl , ketone , group (periodic table) , stereochemistry , medicinal chemistry , organic chemistry
Substituents create access to molecular diversity. Under basic conditions, 6‐azabicyclo[3.2.1]oct‐6‐en‐2‐ones 3 and pyrrolizidines 4 are efficiently synthesized, respectively, in a single step from ethyl isocyanoacetate 2 and divinyl ketones 1 bearing an aryl or alkyl group at the 2‐position. For comparison, only the corresponding pyrrolizidines 4 ′ can be obtained from divinyl ketones 1 ′ bearing a methoxycarbonyl group at the 2‐position.