Asymmetric Synthesis of Chiral N-Sulfinyl 3-Alkyl- and 3-Arylpiperidines by alpha-Alkylation of N-Sulfinyl Imidates with 1-Chloro-3-iodopropane

作者：Colpaert Filip; Mangelinckx Sven; De Kimpe Norbert^*

来源：Journal of Organic Chemistry, 2011, 76(1): 234-244.

DOI：10.1021/jo1020807

alpha-Alkylation of N-sulfinyl imidates with 1-chloro-3-iodopropane successfully led to 2-substituted N-tert-butanesulfinyl-5-chloropentanimidates in acceptable diastereomeric ratios (dr 67/33 to 72/28) and good yields (74-86%). Subsequent reduction with NaBH4 led to the corresponding 2-substituted N-tert-butanesulfinyl-5-chloropentylamines, which could be cyclized to a range of new chiral 3-substituted N-tert-butanesulfinylpiperidines using NaH in DMSO. Finally, the N-tert-butanesulfinylpiperidines could be efficiently deprotected to enantiomerically pure 3-alkyl- and 3-arylpiperidine hydrochlorides.

• 出版日期2011-1-7