Abstract
Remote asymmetric induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived from crotonate and L-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl4 and BF3·OEt2, respectively. The SnCl4-mediated isomerization of silyl dienol ether was found, and the resulting major isomer showed high reactivity to give γ-adduct in high stereoselectivity.
Original language | English |
---|---|
Pages (from-to) | 198-201 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 19 |
Issue number | 1 |
DOIs | |
Publication status | Published - 2017 Jan 6 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry