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Stereodivergent Diversity Oriented Synthesis of Piperidine Alkaloids
Author(s) -
Adriaenssens Louis V.,
Austin Carolyn A.,
Gibson Mairi,
Smith David,
Hartley Richard C.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600744
Subject(s) - chemistry , iminium , reagent , enol , piperidine , organic chemistry , indolizidine , combinatorial chemistry , phenethylamine , enantioselective synthesis , stereochemistry , catalysis , alkaloid
Alkylidenetitanium reagents enable the reagent‐controlled high throughput asymmetric synthesis of 2‐substituted piperidines and rapid access to multiple cyclic imines using solid phase synthesis (SPS). The Schrock carbenes, generated by reduction of thioacetals, convert resin‐bound esters into enol ethers. Treatment with acid releases amino ketones that are cyclized with TMSCl to give iminium salts. Reduction introduces a chiral centre at C‐2, whose absolute stereochemistry is determined by a phenethylamine (PEA) chiral auxiliary. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)