Abstract
Aldol condensation of acetaldehyde and benzaldehyde with the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of one equivalent of triethylborane resulted in the formation of the corresponding 3-hydroxy-2-amino acid ester with excellent stereocontrol (>95% de ) for the formation of syn products. The stereochemical outcome of these reactions is rationalized via the selective formation of the (Z)-enolate of 1 in the presence of triethylborane.
Original language | English (US) |
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Pages (from-to) | 5521-5524 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 32 |
Issue number | 40 |
DOIs | |
State | Published - Sep 30 1991 |
Keywords
- Aldol
- Ester Enolate
- Glycine
- Syn Selectivity
- Triethylborane