Enantio‐ and Diastereoselective 1,2‐Additions to α‐Ketoesters with Diborylmethane and Substituted 1,1‐Diborylalkanes | Zendy

Murray Stephanie A. | Zendy; Green Jacob C. | Zendy; Tailor Sanita B. | Zendy; Meek Simon J. | Zendy

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Enantio‐ and Diastereoselective 1,2‐Additions to α‐Ketoesters with Diborylmethane and Substituted 1,1‐Diborylalkanes

Author(s) -

Murray Stephanie A.,

Green Jacob C.,

Tailor Sanita B.,

Meek Simon J.

Publication year - 2016

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201603465

Subject(s) - stereocenter , enantioselective synthesis , chemistry , phosphine , copper , alkyl , catalysis , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry

The catalytic enantioselective synthesis of boronate‐substituted tertiary alcohols through additions of diborylmethane and substituted 1,1‐diborylalkanes to α‐ketoesters is reported. The reactions are catalyzed by readily available chiral phosphine/copper(I) complexes and produce β‐hydroxyboronates containing up to two contiguous stereogenic centers in up to 99:1 e.r. and greater than 20:1 d.r. The utility of the organoboron products is demonstrated through several chemoselective functionalizations. Evidence indicates the reactions occur via an enantioenriched α‐boryl‐copper‐alkyl intermediate.

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