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 B 0 is synthesized enantioselectively by using the present method as a key step.
Original language | English |
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Pages (from-to) | 442-448 |
Number of pages | 7 |
Journal | Synlett |
Volume | 30 |
Issue number | 4 |
DOIs | |
Publication status | Published - 2019 |
Keywords
- Michael reaction
- asymmetric synthesis
- diastereoselective reaction
- diphenylprolinol silyl ether
- organocatalyst
ASJC Scopus subject areas
- Organic Chemistry