Asymmetric Synthesis of Chiral N-Sulfinyl 3-Alkyl- and 3-Arylpiperidines by α-Alkylation of N-Sulfinyl Imidates with 1-Chloro-3-iodopropane
- 1 December 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (1) , 234-244
- https://doi.org/10.1021/jo1020807
Abstract
α-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 NaBH(4) 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.Keywords
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