DIASTEREOSELECTIVE ALKYLATION OF THE DIANION OF 5-ETHOXY-4(S)-HYDROXY-1-ISOPROPYL-2-PYRROLIDINONE; SHYNTHESIS OF ENANTIOMERICALLY PURE AZABICYCLES

DOI: 10.1016/S0040-4039(01)81047-9

Source and publish data:

Tetrahedron Letters p. 1581 - 1584 (1987)

Update date:2022-09-26

Topics:

Authors:

Klaver, Wim J.

Hiemstra, Henk

Speckamp, Nico

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Article abstract of DOI:10.1016/S0040-4039(01)81047-9

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).

Full text of DOI:10.1016/S0040-4039(01)81047-9

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