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Phosphine‐Initiated Cascade Annulation of β′‐Acetoxy Allenoate and p ‐Quinols: Access to Ring Fused Hexahydroindeno Furan Derivatives
Author(s) -
Xing JiaoJiao,
Gao YuNing,
Shi Min
Publication year - 2018
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.201800319
Subject(s) - annulation , stereocenter , chemistry , furan , phosphine , ring (chemistry) , cascade , cascade reaction , combinatorial chemistry , stereochemistry , catalysis , medicinal chemistry , enantioselective synthesis , organic chemistry , chromatography
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.