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Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration.
Alam, Rauful; Vollgraff, Tobias; Eriksson, Lars; Szabó, Kálmán J.
Affiliation
  • Alam R; Department of Organic Chemistry and ‡Department of Materials and Environmental Chemistry, Stockholm University , SE-106 91 Stockholm, Sweden.
  • Vollgraff T; Department of Organic Chemistry and ‡Department of Materials and Environmental Chemistry, Stockholm University , SE-106 91 Stockholm, Sweden.
  • Eriksson L; Department of Organic Chemistry and ‡Department of Materials and Environmental Chemistry, Stockholm University , SE-106 91 Stockholm, Sweden.
  • Szabó KJ; Department of Organic Chemistry and ‡Department of Materials and Environmental Chemistry, Stockholm University , SE-106 91 Stockholm, Sweden.
J Am Chem Soc ; 137(35): 11262-5, 2015 Sep 09.
Article in En | MEDLINE | ID: mdl-26316158
ABSTRACT
Allylboration of ketones with γ-disubstituted allylboronic acids is performed in the presence of chiral BINOL derivatives. The reaction is suitable for single-step creation of adjacent quaternary stereocenters with high selectivity. We show that, with an appropriate choice of the chiral catalyst and the stereoisomeric prenyl substrate, full control of the stereo- and enantioselectivity is possible in the reaction.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Am Chem Soc Year: 2015 Document type: Article Affiliation country: Sweden
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Add to My VHL
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Am Chem Soc Year: 2015 Document type: Article Affiliation country: Sweden