Davis, Franklin A. ; Prasad, Kavirayani R. ; Carroll, Patrick J. (2002) Asymmetric synthesis of polyhydroxy α-amino acids with the sulfinimine-mediated asymmetric strecker reaction: 2-amino 2-deoxyl-xylono-1,5-lactone (polyoxamic acid lactone) The Journal of Organic Chemistry, 67 (22). pp. 7802-7806. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo020302e
Related URL: http://dx.doi.org/10.1021/jo020302e
Abstract
Polyhydroxylated sulfinimines derived from protected 1,2-O-isopropyliden-l-threoses undergo the sulfinimine-mediated Strecker syntheses to give α-amino nitriles in good yield and de. A double stereodifferentiation effect was not observed and the diastereoselectivity is controlled by the absolute configuration of the sulfinyl group. Hydrolysis of the amino nitriles afforded the lactone rather than polyoxamic acid.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 106038 |
| Deposited On: | 21 Dec 2017 12:02 |
| Last Modified: | 21 Dec 2017 12:02 |
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