Phosphine‐Initiated Cascade Annulation of β′‐Acetoxy Allenoate and p‐Quinols: Access to Ring Fused Hexahydroindeno Furan Derivatives

A highly diastereoselective cascade annulation process of p‐quinols with β′‐acetoxy allenoate catalyzed by phosphine has been developed, which comes up with highly functionalized multiple ring‐fused hexahydroindeno furan derivatives in synthetically useful yields and creates three consecutive stereo...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-07, Vol.360 (13), p.2552-2559
Main Authors: Xing, Jiao‐Jiao, Gao, Yu‐Ning, Shi, Min
Format: Article
Language:English
Subjects:
cascade annulation
Cascade chemical reactions
Chemical reactions
Derivatives
Functional groups
Organic chemistry
p-quinols
phosphine catalyst
ring-fused hexahydroindeno furan derivatives
Stereoselectivity
Substrates
β′-acetoxy allenoate
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Summary:A highly diastereoselective cascade annulation process of p‐quinols with β′‐acetoxy allenoate catalyzed by phosphine has been developed, which comes up with highly functionalized multiple ring‐fused hexahydroindeno furan derivatives in synthetically useful yields and creates three consecutive stereogenic carbon centers only in a one‐step manner. The salient features of this phosphine‐catalyzed cyclization include the use of p‐quinol's three active sites in this cascade reaction, wide substrate scope, excellent functional group tolerance, mild reaction conditions, asymmetric version, good yields, ease of scale‐up to gram scale, and further transformations.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800319