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 | Zendy

Wang Chen | Zendy; Mao ZhuoYa | Zendy; Liu YiWen | Zendy; Wang QiaoE | Zendy; Si ChangMei | Zendy; Wei BangGuo | Zendy; Lin GuoQiang | Zendy

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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).

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