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Synthesis of peptide thiazolines from β-hydroxythioamides. An investigation of racemization in cyclodehydration protocols

✍ Scribed by Peter Wipf; Paul C. Fritch

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 298 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73509-x

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✦ Synopsis

The formation of thiezolines from &hydroxythioamides under TsCUEbN, SOCi2. snd Mitsunobu conditions leads to extensive epimerlzatlon at the C(2) exo methine position. in contrast. thiardines of >94% diastereomeric purity are isolated when the Burgess cyciodehydration protocol is eppiied.

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