Tetrahedron Letters p. 1581 - 1584 (1987)
Update date:2022-09-26
Topics:
Klaver, Wim J.
Hiemstra, Henk
Speckamp, Nico
The alkylation of the dianion of the title compound (2), readily prepared from (S)-malic acid, with ω-iodo-1-trimethylsilyl-2-alkynes (8a-c) occurs with high trans-selectivity with respect to the hydroxyl function.The products (11a-c) cyclize in formic acid to enantiomerically pure azabicyclic allenes (12a-c), one of which (12b) might be a suitable precursor to peduncularine (15).
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Doi:10.1016/S0040-4020(01)81663-X
(1987)Doi:10.1021/jm00397a025
(1988)Doi:10.1016/S0040-4039(00)95819-2
(1987)Doi:10.1016/j.tet.2008.11.092
(2009)Doi:10.1016/S0040-4039(00)95465-0
(1987)Doi:10.1021/ja00256a069
(1987)
