The first asymmetric total syntheses of 3((1R,2R)- and 3((1S,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid
β Scribed by Mohapatra, Debendra K.; Guguloth, Nagesh; Yadav, J.S.
- Book ID
- 125475517
- Publisher
- Elsevier Science
- Year
- 2012
- Tongue
- French
- Weight
- 509 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
The first asymmetric synthesis of (2S)-, and (2R)-amino-3,3-dimethoxypropanoic acid (a-formylglycine dimethylacetal) has been achieved in two steps and 91% overall yield. The key step involved the quenching of a chiral glycine titanium enolate with trimethyl orthoformate.
Addition of diethyl phosphite to 2,3-O-cyclohexylidene-D-glyceraldehyde catalyzed by triethylamine or fluorides led to ca. 35:65 mixtures of diethyl (IR,2R)-and (1S,2R)-2,3-O-cyclohexylidene-l,2,3trihydroxypropylphosphonates (4a) and (4b). Application of lithium diethylphosphonate only slightly impr