Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives

• Akiyama, Sota

• Kubota, Koji

• Mikus, Malte S.

• Paioti, Paulo H. S.

• Romiti, Filippo

• Liu, Qinghe

• Zhou, Yuebiao

• Hoveyda, Amir H.

• Ito, Hajime

抄録

The first catalytic method for diastereo- and enantioselective synthesis of allylic boronates bearing a Z-trisubstituted alkenyl fluoride is disclosed. Boryl substitution is performed with either a Z- or E-allyldifluoride and is catalyzed by bisphosphine/Cu complexes, affording products in up to 99 % yield with >98:2 Z/E selectivity and 99:1 enantiomeric ratio. A variety of subsequent modifications are feasible, and notable examples are diastereoselective additions to aldehydes/aldimines to access homoallylic alcohols/amines containing a fluorosubstituted stereogenic quaternary center.

収録刊行物

• Angewandte chemie-international edition

  Angewandte chemie-international edition 58 (35), 11998-12003, 2020-06-13

  Wiley-Blackwell

キーワード

• boron
• copper
• enantioselective catalysis
• fluorine
• synthetic methods

詳細情報

• CRID: 1050848249909500672
• NII論文ID: 120006880722
• HANDLE: 2115/79109
• ISSN: 14337851
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles