Diastereoselective strecker synthesis using α-phenylglycinol as chiral auxiliary
✍ Scribed by T.K. Chakraborty; G.V. Reddy; K. Azhar Hussain
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 270 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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## Abstract The asymmetric synthesis of __N__‐galactosyl D‐α‐amino nitriles is accomplished by application of 2,3,4,6‐tetra‐__O__‐pivaloyl‐β‐D‐galactopyranosylamine (4) as the stereodifferentiating template in Strecker reactions. Aldimines 6 derived from 4 and aromatic or aliphatic aldehydes react
The reduction of a-keto esters derived from (IL)-1,2;5,6-biscyclohexylidene-3-terrbutyldimethysilyl-chiro -inositol with Selectride@ proceeded with high diastereoselectivity to afford the corresponding a-hydroxy esters. Addition of l&Crown-6 led to dramatic changeover in diastereofacial selectivity.
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