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Construction of All‐Carbon Chiral Quaternary Centers through Cu I ‐Catalyzed Enantioselective Reductive Hydroxymethylation of 1,1‐Disubstituted Allenes with CO 2
Author(s) -
Qiu Jia,
Gao Shen,
Li Chaopeng,
Zhang Lei,
Wang Zheng,
Wang Xiaoming,
Ding Kuiling
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903906
Subject(s) - enantioselective synthesis , catalysis , chemistry , alcohol , quaternary carbon , reductive elimination , copper , organic chemistry , medicinal chemistry , combinatorial chemistry
A catalytic enantioselective construction of all‐carbon chiral quaternary centers through reductive hydroxymethylation of 1,1‐disubstituted allenes with CO 2 has been developed. In the presence of a copper/Mandyphos catalyst, CO 2 is transformed into an alcohol oxidation level by an asymmetric reductive C−C bond formation with allenes by using hydrosilane (HSi(OMe) 2 Me) as a reductant. The resulting chiral homoallylic alcohols are versatile synthetic intermediates and can be conveniently converted into a variety of useful chiral chemicals.