ISSN:
0170-2041
Keywords:
Aziridines
;
Amino acids
;
Wittig olefination
;
Glyceraldehyde
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Chemistry of Aziridine Carboxylic Acids, V. - Asymmetric Synthesis of Enantiomerically Pure Aziridine Carboxylic Acid Derivatives from (R)- and (S)-Glyceraldehyde AcetonideThe α-bromoacrylic acid derivatives 2 reacted with benzylamine by ring closure to cis-aziridines 3 and trans-aziridines 4 with ≥99% diastereomeric excess. The aziridines 3 and 4 were hydrogenated by LiAlH4 to give alcohols 5 and 6. Tosylations of 6 yielded the crystalline sulfonamides 7. The absolute configurations of (2R,3S,4R)-3c, (2S,3R,4S)-5and (1R,2R,4R)-7 were determined by X-ray analyses.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419941010
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