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2005
Azetidine derivatives
R 0045
Synthesis and Reactivity of Enantiomerically Pure N-Alkyl-2-alkenyl Azetidinium Salts. — Enantiopure stereodefined 2-alkenyl azetidines such as (III) are prepared
03- 109 using
Wittig olefination as the key step. Their stereoselective conversion to quaternary
triflate salts is achieved with TmsOTf. Stevens rearrangement of salts (V) leads to
3-alkenyl pyrrolidines. Interestingly, reaction of triflate (Va) with phenyllithium results
in an unprecedented SN2' reaction yielding the ring-open product (VIII). —
(COUTY*, F.; DURRAT, F.; EVANO, G.; PRIM, D.; Tetrahedron Lett. 45 (2004) 40,
7525-7528; SIRCOB, CNRS, Univ. Versailles, F-78035 Versailles, Fr.; Eng.) — Mais
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