Abstract
Figure presented The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block undergoes efficient and highly diastereoselective lithium enolate Michael additions to α,β-unsaturated ketones, lactones, and nitro olefins. Subsequent deprotection of these Michael adducts gives α-hydroxy acids in very high yield. Hydrogenation of the nitro group in some of the adducts leads to γ-lactams, which can be easily converted into α-hydroxy-γ-amino acid derivatives.
Original language | English |
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Pages (from-to) | 3753-3755 |
Number of pages | 2 |
Journal | Organic Letters |
Volume | 3 |
Issue number | 23 |
DOIs | |
Publication status | Published - 15 Nov 2001 |
Keywords
- Stereoselective synthesis (diastereoselective Michael addn. of butanediacetal desymmetrized glycolic acid to a,b-unsatd. ketones, lactones, and nitro olefins and prepn. of a-hydroxy-g-amino acid derivs.); Michael reaction (stereoselective; diastereoselective Michael addn. of butanediacetal desymmetrized glycolic acid to a,b-unsatd. ketones, lactones, and nitro olefins and prepn. of a-hydroxy-g-amino acid derivs.)