Stereoselective Allyl Amine Synthesis through Enantioselective Addition of Diethylzinc and [1,3]‐Chirality Transfer: Synthesis of Lentiginosine and Polyoxamic Acid Derivative
- 25 February 2005
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 11 (6), 1949-1957
- https://doi.org/10.1002/chem.200400830
Abstract
A new synthetic method for the preparation of allyl amines has been developed. The key steps of this method are enantioselective addition of diethylzinc and [1,3]-chirality transfer through the [3.3] sigmatropic rearrangement of allyl cyanates. Stereocontrolled syntheses of lentiginosine (1) and polyoxamic acid derivative 2 from a common intermediate 7 derived from D-tartaric acid (8), have been accomplished.Keywords
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