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The conjugate addition of lithium (R)-N-phenyl-N-(α-methylbenzyl)amide to a range of α,β-unsaturated 4-methoxyphenyl esters proceeds with excellent levels of diastereoselectivity to give the corresponding β-amino esters in good yield and as single diastereoisomers (>99:1 dr). The synthetic utility of this methodology has been demonstrated via the short and concise asymmetric synthesis of the tetrahydroquinoline alkaloid (R)-(-)-angustureine in six steps and 32% overall yield from commercially available oct-2-enoic acid.

Original publication

DOI

10.1021/ol200625h

Type

Journal article

Journal

Org Lett

Publication Date

20/05/2011

Volume

13

Pages

2544 - 2547

Keywords

Alkaloids, Fatty Acids, Monounsaturated, Lithium, Molecular Structure, Organometallic Compounds, Quinolines, Stereoisomerism