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Inherently Chiral Calix[4]arenes: A Chiral Sulfoxide as an Ortholithiation Director
Author(s) -
Castell Dominic C.,
Lesotho Ntlama,
Nikolayenko Varvara I.,
Arnott Gareth E.
Publication year - 2017
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.201700701
Subject(s) - sulfoxide , diastereomer , chemistry , calixarene , stereochemistry , combinatorial chemistry , organic chemistry , molecule
In pursuit of nonracemic, inherently chiral calix[4]arenes, we describe herein the application of a chiral tert ‐butyl sulfoxide in asymmetrically directing ortholithiation on a calix[4]arene. We demonstrate good diastereoselectivity ( dr = 95:5) in the reaction, and also provide proof of the major diastereomer through single‐crystal X‐ray diffraction.