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Copper‐Catalyzed Asymmetric Three‐Component Borylstannation: Enantioselective Formation of CSn Bond
Author(s) -
Jia Tao,
Cao Peng,
Wang Ding,
Lou Yazhou,
Liao Jian
Publication year - 2015
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.201500060
Subject(s) - transmetalation , enantioselective synthesis , tandem , chemistry , aryl , enantiomer , catalysis , combinatorial chemistry , copper , alkyl , component (thermodynamics) , stereochemistry , organic chemistry , materials science , physics , composite material , thermodynamics
In summary, a first copper‐catalyzed synthesis of α‐aryl‐β‐borylstannane compounds was accomplished through three‐component borylstannation of aryl‐substituted alkenes. In the exploration of an asymmetric variant, chiral sulfinylphosphine ligands proved advantageous in controlling stereochemistry of BCu addition and in promoting transmetalation of enantioenriched alkylCu species. The stereochemical outcome supported a sequential syn ‐borylcupration and configuration‐retentive transmetalation mechanism. Moreover, α‐chiral β‐borylstannanes were easily transformed into a diverse array of secondary alkylstannanes and triarylethane with high enantiomeric purity. The applications of chiral sulfinylphosphine ligands to other tandem CuB addition reactions are currently under investigation in our group.