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CC BY-ND-NC 4.0 · Synlett 2019; 30(04): 442-448
DOI: 10.1055/s-0037-1611644
DOI: 10.1055/s-0037-1611644
letter
Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl Ether
JSPS KAKENHI grant number JP18H04641: Hybrid Catalysis for Enabling Molecular Synthesis on Demand, and The Uehara Memorial Foundation.Further Information
Publication History
Received: 30 August 2018
Accepted after revision: 03 December 2018
Publication Date:
16 January 2019 (online)
Published as part of the 30 Years SYNLETT – Pearl Anniversary Issue
Abstract
An efficient synthetic route to install chiral 1,3-dimethyl units through a double Michael reaction of crotonaldehyde and nitromethane catalyzed by diphenylprolinol silyl ether is developed. Either 1,3-syn- or 1,3-anti-dimethyl units are obtained selectively depending on the enantiomer of the diphenylprolinol silyl ether catalyst used. The side chain of pneumocandin B0 is synthesized enantioselectively by using the present method as a key step.
Key words
organocatalyst - Michael reaction - asymmetric synthesis - diastereoselective reaction - diphenylprolinol silyl etherSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611644.
- Supporting Information
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