Issue 19, 2023

Synthesis of (Z)-alkenyl boronates via a copper(i)-catalyzed linear-selective alkylboration of terminal allenes

Abstract

A copper(I)-catalyzed intermolecular alkylboration of terminal allenes using unactivated alkyl iodides as the carbon electrophiles is reported. The regio- and stereochemistry of the product, (Z)-alkenyl boronate, could be constructed without the need to introduce directing groups. A wide range of terminal allenes substituted with prim-, sec- and tert-alkyl groups as well as heteroatoms are suitable for this reaction. Furthermore, the product can be used for the stereoselective synthesis of multi-substituted alkenes via Suzuki–Miyaura cross-coupling reactions. We also demonstrate the formal total synthesis of the marine natural product schizol A by means of the alkylboration of a terminal allene as the key step for the construction of the alkene moiety bearing two alkyl groups in a cis orientation. The direct precursor of schizol A was obtained with perfect stereoselectivity.

Graphical abstract: Synthesis of (Z)-alkenyl boronates via a copper(i)-catalyzed linear-selective alkylboration of terminal allenes

Supplementary files

Article information

Article type
Research Article
Submitted
19 iyl 2023
Accepted
07 avq 2023
First published
10 avq 2023

Org. Chem. Front., 2023,10, 4786-4793

Author version available

Synthesis of (Z)-alkenyl boronates via a copper(I)-catalyzed linear-selective alkylboration of terminal allenes

Y. Ozawa, Y. Shiratori, H. Koriyama, K. Endo, H. Iwamoto and H. Ito, Org. Chem. Front., 2023, 10, 4786 DOI: 10.1039/D3QO01095C

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