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DOI: 10.1055/s-2007-991472
Asymmetric Synthesis of Oxazolidines, Thiazolidines, and Pyrrolidines
V. Sriramurthy, G. A. Barcan, O. Kwon*
University of California, Los Angeles, USA
Publication History
Publication Date:
18 December 2007 (online)

Significance
An efficient methodology for the asymmetric synthesis of oxazolidines, thiazolidines, pyrrolidines and octahydroindoles by a DPPP-catalyzed reaction of β -amino alcohols, β -amino thiols or γ-amino malonates with terminal acetylenes is reported. Of the phosphine catalysts tested (DPPP, DPPM, DPPE, DPPB, Ph3P, Ph2PEt, Me3P), DPPP demonstrated the highest activity. A mechanism is proposed which proceeds with a double Michael addition to an electron-deficient acetylene to afford intermediate A which, upon intramolecular SN2 cyclization, leads to the final product. The scope of the reaction was inadequately explored.