- Electrophilic ring opening of oxazolines derived from serine and threonine: A practical entry to N(N)-protected β-halogeno α-aminoesters
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Treatment of oxazolines 4a-c derived from serine or threonine with chloroformates, leads to the oxazoline ring opening and to the formation of N,N-protected β-chloro-α-aminoesters la-e in 30-88% isolated yields. In the presence of NaI (0.9 equiv), oxazolines 4a,b,d react with ethyl chloroformate to afford the N,N-protected β-iodo α-amino esters 1f-h (67-89% yields), whereas the reaction of 4a,b with trimethylsilyl halide gives the analogous N-benzoyl β-halogeno derivatives 1i,k with 30-86% yields.
- Laaziri, Abdelhamid,Uziel, Jacques,Juge, Sylvain
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p. 437 - 447
(2007/10/03)
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