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Synthesis 2014; 46(10): 1367-1373
DOI: 10.1055/s-0033-1340901
DOI: 10.1055/s-0033-1340901
special topic
Asymmetric α-Allylation of α-Branched Aldehydes with Allyl Alcohols by Synergistic Catalysis Using an Achiral Palladium Complex and a Chiral Primary Amino Acid
Further Information
Publication History
Received: 26 December 2013
Accepted after revision: 12 February 2014
Publication Date:
17 March 2014 (online)
Abstract
Highly enantioselective direct α-allylation of α-branched aldehydes with simple allyl alcohols was achieved by the combined use of an achiral transition-metal catalysis with a palladium complex and a chiral organocatalysis with a readily obtainable primary α-amino acid. Various α-allylated aldehydes possessing a stereocontrolled quaternary carbon stereogenic center were synthesized in high yields with high enantioselectivity.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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Selected reviews on organocatalytic asymmetric Michael addition:
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Selected reviews on Tsuji–Trost allylation reaction:
Reviews on catalysis by combined use of organocatalysts and transition-metal catalysts:
Enantioselective allylation of enamines:
O-Silylated l-serines and l-threonines:
O-Silylated β-homoserine: