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| - 2-Trimethylsilylethanesulfonyl (SES) versus Tosyl(Ts) Protecting Group in the Preparation ofNitrogen-Containing Five-Membered Rings. ANovel Route for the Synthesis of SubstitutedPyrrolines and Pyrrolidines
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| - The 2-trimethylsilylethanesulfonyl (or SES) protecting groupwas compared to the tosyl (Ts) group in the preparation ofa nitrogen-containing five-membered ring obtained by theaza-Baylis−Hillman/alkylation/RCM route. While deprotection of Ts-protected pyrrolines gave only pyrroles, deprotection of the same SES-protected compounds gave eitherpyrroles or free amine pyrrolines depending on the deprotection conditions. The SES-protected pyrrolines were hydrogenated to yield pyrrolidines with an excellent diastereoselectivity. Free amine pyrrolidines were obtained by HF-mediated deprotection of the SES group.
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