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Construction of Functionalized Carbocycles Having Contiguous Tertiary Carbinol and All‐Carbon Stereogenic Centers
Author(s) -
Reddy Chennakesava,
Babu Srinivasarao Arulananda,
Aslam Nayyar Ahmad,
Rajkumar Vadla
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201382
Subject(s) - stereocenter , chemistry , propargyl , stereoselectivity , selectivity , bicyclic molecule , stereochemistry , asymmetric induction , crystal structure , organic chemistry , enantioselective synthesis , catalysis
A highly stereoselective protocol is reported for customizing functionalized carbocyclic building blocks (β‐hydroxy esters) and bicyclic lactones with a stereoarray that contains contiguous tertiary carbinol and all‐carbon stereocenters. The efficient asymmetric induction and diastereofacial selective addition of allyl and propargyl indiums to hindered α,α‐disubstituted cycloalkanones is presented. The stereochemistry of representative products was unequivocally established from single‐crystal X‐ray crystal structure analyses, and a plausible reaction pathway was proposed to support the high diastereofacial selectivity.