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Organocatalytic Asymmetric Hydrophosphination of α,β‐Unsaturated Aldehydes: Development, Mechanism and DFT Calculations
Author(s) -
Ibrahem Ismail,
Hammar Peter,
Vesely Jan,
Rios Ramon,
Eriksson Lars,
Córdova Armando
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800277
Subject(s) - chemistry , enantioselective synthesis , nucleophile , phosphine , organocatalysis , optically active , computational chemistry , mechanism (biology) , density functional theory , catalysis , organic chemistry , diphenylphosphine , combinatorial chemistry , philosophy , epistemology
The development and mechanism of the highly chemo‐ and enantioselective organocatalytic hydrophosphination reaction of α,β‐unsaturated aldehydes is presented. The reactions are catalyzed by protected chiral diarylprolinol derivatives and give access to optically active phosphine derivatives in high yields with up to 99% ee . The organocatalytic addition of other phosphorus nucleophiles was also investigated. The origin of the high enantioselectivity for the reaction with diphenylphosphine as the nucleophile is investigated by density functional theory calculations.