Rational and practical synthesis of α,α-difluoro-γ-lactams
✍ Scribed by Bin-Hui Li; Ke-Lai Li; Qing-Yun Chen
- Book ID
- 113711596
- Publisher
- Elsevier Science
- Year
- 2012
- Tongue
- English
- Weight
- 300 KB
- Volume
- 133
- Category
- Article
- ISSN
- 0022-1139
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## Abstract For Abstract see ChemInform Abstract in Full Text.
## Abstract The synthesis of __gem__‐difluorinated β‐lactams and __gem__‐difluorinated β‐amino acids, each possessing a potential basic functional group, from ethyl bromodifluoroacetate and either imines (for β‐lactams) or __N__‐(α‐aminoalkyl)benzotriazoles (for β‐amino esters) was investigated. A
Reformatsky reaction of ethyl bromodifluoroacetate with N,N-(dibenzyl)-1H-benzotriazolyl-1-methylamine gave fully protected a,a-difluoro-b-alanine. Hydrogenolysis and hydrolysis furnished a,a-difluoro-b-alanine. Further transformation into N-phthalimido-a,a-difluoro-b-alanine was described.
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