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Short Paper | Special issue | Vol 84, No. 2, 2012, pp.1289-1299
Published online, 29th August, 2011
DOI: 10.3987/COM-11-S(P)47
An Improved Synthesis of Functionalized cis-Decahydroquinolines Using a Baylis-Hillman-Type Adduct

Junfeng Huang, Jeffrey Petersen, and Stephen C. Bergmeier*

*Department of Chemistry and Biochemistry, Ohio University, Clippinger Laboratories, Athens, OH 45701-2979, U.S.A.

Abstract

An efficient and diastereoselective method to synthesize highly functionalized cis-decahydroquinolines was reported. The addition of a vinyl aluminum reagent to an aldehyde followed by an intramolecular SN2’ Mitsunobu reaction gave the desired 3,7,8-trisubstituted product designed as methyllycaconitine analogs. An unexpected tandem vinylaluminum addition and Michael reaction to produce a 4-hydroxy cis-decahydroquinoline has also been reported.