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Stereoselective Intermolecular [4+2] Process of N ,O‐acetals with Terminal Alkynes for Construction of Functional cis ‐Pyrido and Pyrrolo[1,2‐c][1,3]oxazin‐1‐ones
Author(s) -
Wang Chen,
Mao ZhuoYa,
Liu YiWen,
Wang QiaoE,
Si ChangMei,
Wei BangGuo,
Lin GuoQiang
Publication year - 2020
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.201901141
Subject(s) - chemistry , yield (engineering) , stereoselectivity , acetal , stereochemistry , intermolecular force , terminal (telecommunication) , catalysis , molecule , organic chemistry , computer science , materials science , metallurgy , telecommunications
A diastereoselective approach to access cis‐ pyrido and pyrrolo[1,2‐c][1,3]oxazin‐1‐ones has been developed through a one‐pot BF 3 . Et 2 O‐catalyzed [4+2] process starting with N ,O‐acetals and terminal alkynes. In addition, the utility of this transformation is demonstrated by the scalable synthesis of (+)‐Febrifugine in 7 steps from the N ,O‐acetal (15% overall yield).