4.4 Article

Tertiary Alkylations of Aldehydes, Ketones or Imines Using Benzylic Organoboronates and a Base Catalyst

Journal

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 93, Issue 9, Pages 1065-1069

Publisher

CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20200122

Keywords

Base catalyst; Organoboron; 1,2-Addition

Funding

  1. JSPS KAKENHI [JP17H06449, JP18H01971]
  2. Kanazawa University SAKIGAKE project 2018

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The KHMDS-catalyzed tertiary alkylation of aldehydes, ketones or imines using tertiary benzylic organoboronates is reported. This protocol permitted the use of tertiary benzylic alkylboronates as the tertiary alkyl anion for construction of highly congested contiguous sp(3) carbon centers. The mild and transition-metal-free reaction conditions are attractive features of the protocol.

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