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Issue 7, 2005
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Cyclic β-amino acid derivatives: synthesis vialithium amide promoted tandem asymmetric conjugate addition–cyclisation reactions

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Abstract

The product distribution upon conjugate addition of homochiral lithium N-benzyl-N-α-methylbenzylamide to dimethyl-(E,E)-nona-2,7-dienedioate can be controlled to give either the cyclic 1,2-anti-1,6-anti-β-amino ester (derived from conjugate addition and intramolecular enolate cyclisation) or the acyclic bis-β-amino ester derivative (derived from double conjugate addition) in high de. The introduction of a protected nitrogen functionality into the diester skeleton facilitates, after conjugate addition and intramolecular enolate cyclisation, the asymmetric construction of piperidines in high de; variation in the N-protecting group indicates that the highest stereoselectivity is observed with α-branched N-substituents. Tandem conjugate addition–aldol reactions can also be achieved stereoselectively, with lithium amide conjugate addition to ε- and ζ-oxo-α,β-unsaturated esters giving the corresponding five and six membered cyclic β-amino esters in high de. N-deprotection by hydrogenolysis of the products arising from these reactions furnishes a range of polyfunctionalised transpentacin and transhexacin derivatives in high de and ee.

Graphical abstract: Cyclic β-amino acid derivatives: synthesis via lithium amide promoted tandem asymmetric conjugate addition–cyclisation reactions

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Article information


Submitted
07 Jan 2005
Accepted
01 Feb 2005
First published
02 Mar 2005

Org. Biomol. Chem., 2005,3, 1284-1301
Article type
Paper

Cyclic β-amino acid derivatives: synthesis via lithium amide promoted tandem asymmetric conjugate addition–cyclisation reactions

S. G. Davies, D. Díez, S. H. Dominguez, N. M. Garrido, D. Kruchinin, P. D. Price and A. D. Smith, Org. Biomol. Chem., 2005, 3, 1284
DOI: 10.1039/B500223K

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