在含氮五元环制备中2-三甲基硅基乙磺酰基（SES）与对甲苯磺酰基（Ts）保护基的比较。一种合成取代吡咯啉和吡咯烷的新途径。

2-Trimethylsilylethanesulfonyl (SES) versus tosyl (Ts) protecting group in the preparation of nitrogen-containing five-membered rings. A novel route for the synthesis of substituted pyrrolines and pyrrolidines.

作者信息

Declerck Valérie, Allouchi Hassan, Martinez Jean, Lamaty Frédéric

机构信息

Laboratoire des Aminoacides, Peptides et Protéines (LAPP), CNRS, Universités Montpellier 1 et 2, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.

出版信息

J Org Chem. 2007 Feb 16;72(4):1518-21. doi: 10.1021/jo062239p.

DOI:10.1021/jo062239p

PMID:17288397

Abstract

The 2-trimethylsilylethanesulfonyl (or SES) protecting group was compared to the tosyl (Ts) group in the preparation of a nitrogen-containing five-membered ring obtained by the aza-Baylis-Hillman/alkylation/RCM route. While deprotection of Ts-protected pyrrolines gave only pyrroles, deprotection of the same SES-protected compounds gave either pyrroles 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.

摘要

在通过氮杂-Baylis-Hillman/烷基化/关环复分解反应路线制备含氮五元环的过程中，将2-三甲基硅基乙磺酰基（或SES）保护基与对甲苯磺酰基（Ts）保护基进行了比较。虽然Ts保护的吡咯啉脱保护仅得到吡咯，但相同的SES保护的化合物脱保护根据脱保护条件可得到吡咯或游离胺吡咯啉。SES保护的吡咯啉被氢化以优异的非对映选择性生成吡咯烷。通过HF介导的SES基团脱保护得到游离胺吡咯烷。