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Electrophilic Addition of Allylic Carbocations to 2‐Cyclopropylidene‐2‐arylethanols: A Strategy to 3‐Oxabicyclo[3.2.0]heptanes
Author(s) -
Meng Bo,
Huang Xian,
Wu Luling
Publication year - 2013
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.201201073
Subject(s) - carbocation , allylic rearrangement , chemistry , electrophile , intramolecular force , ring (chemistry) , electrophilic addition , medicinal chemistry , stereochemistry , organic chemistry , catalysis
We have developed an electrophilic addition of allylic carbocations to 2‐cyclopropylidene‐2‐arylethanols constructing carbon‐carbon bonds with excellent regio‐ and stereoselectivities. The reaction affords 3‐oxabicyclo[3.2.0]heptanes in moderate to good yields via the electrophilic addition/ring‐opening/vinyl group shift/intramolecular cyclization sequence.