Abstract
α-Hydroxy acids have been reacted with bis-dihydropyrans to give dispiroketal adducts (1,8,13,16-tetraoxadispiro[5.0.5.4]-hexadecan-14-ones). The enolates derived from these compounds undergo reaction with electrophiles with generally high levels of diastereoselectivity. Subsequent deprotection of these compounds gives α-hydroxy esters of high enantiomeric excess.
Original language | English |
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Pages (from-to) | 7157-7176 |
Number of pages | 20 |
Journal | Tetrahedron |
Volume | 50 |
Issue number | 24 |
DOIs | |
Publication status | Published - 1 Jan 1994 |
Externally published | Yes |
Funding
Acknowledgements We thank the SERC (MW, RD). KOSEF (KSK) and the Ron~soy Menlorial Fund (G-JB) for financial support. We also gratefully acknowledge the B.P. endowment (to SVL) ut Cambridge.