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Synlett 2019; 30(10): 1105-1110
DOI: 10.1055/s-0037-1611728
DOI: 10.1055/s-0037-1611728
synpacts
Deoxygenative Transformation of Carbonyl and Carboxyl Compounds Using gem-Diborylalkanes
This work was supported by the National Natural Science Foundation of China (Grant no. 91745110, 21673261, 21603245, 21633013, 21703265, 21872156 and 21802150), Natural Science Foundation of Jiangsu Province (Grant no. BK20181194, BK20180247), and a start-up funding from LICP. Support from the Young Elite Scientist Sponsorship Program by CAST, the Youth Innovation Promotion Association CAS (2018458).
Further Information
Publication History
Received: 10 January 2019
Accepted after revision: 23 January 2019
Publication Date:
21 February 2019 (online)
Abstract
gem-Diborylalkanes serve as privileged carbanion precursors for the efficient construction of carbon–carbon bond with various carbonyl and carboxyl compounds. We highlight the recent advances on deoxygenative transformation of carbonyl and carboxyl compounds using gem-diborylalkanes reagents. Our recent development of a dual functionalization of gem-diborylalkanes through deoxygenative enolization with the carboxylic acids is also discussed.
1 Introduction
2 Activation Modes of gem-Diborylalkanes
3 Deoxygenative Transformation of Carbonyl and Carboxyl Compounds via α-Diboryl Carbanion
3.1 Reaction with Aldehyde and Ketone Electrophiles
3.2 Reaction with Carboxylic Acid Derivatives
4 Deoxygenative Transformation of Carbonyl and Carboxyl Compounds via α-Monoboryl Carbanion
5 Conclusion
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