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Synthesis and Application of Chiral Phosphorus Ligands Derived from T ADDOL for the Asymmetric Conjugate Addition of Diethyl Zinc to Enones
Author(s) -
Alexakis Alexandre,
Burton Jonathan,
Vastra Johann,
Benhaim Cyril,
Fournioux Xavier,
van den Heuvel Alexandra,
Levêque JeanMarc,
Mazé Frédérique,
Rosset Stephane
Publication year - 2000
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 - 10.1002/1099-0690(200012)2000:24<4011::aid-ejoc4011>3.0.co;2-d
Subject(s) - chemistry , diethylzinc , conjugate , substituent , chalcone , trifluoromethanesulfonate , enantiomer , zinc , asymmetric induction , enantioselective synthesis , organic chemistry , medicinal chemistry , catalysis , mathematical analysis , mathematics
Asymmetric conjugate addition of diethylzinc to cyclohexen‐2‐one, chalcone, and benzalacetone has been found to occur with 0.5% copper(II) triflate and 1% chiral phosphite. Cyclic phosphites derived from T ADDOL gave excellent to moderate enantiomeric excesses. The nature of the exocyclic substituent of the dioxaphospholane ring is important, but the chiral induction is imposed by the T ADDOL framework. Syntheses of all the T ADDOL ligands are described.