Conjugate addition of lithium N-phenyl-N-(α-methylbenzyl)amide: application to the asymmetric synthesis of (R)-(-)-angustureine.

Bentley, SA; Davies, SG; Lee, JA; Roberts, PM; Thomson, JE

Abstract:

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.

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APA Style

Bentley, S. A., Davies, S. G., Lee, J. A., Roberts, P. M., & Thomson, J. E. (2011). Conjugate addition of lithium N-phenyl-N-(α-methylbenzyl)amide: application to the asymmetric synthesis of (R)-(-)-angustureine. Organic Letters, 13(10), 2544–2547.

MLA Style

Bentley, S. A., et al. “Conjugate Addition of Lithium N-Phenyl-N-(α-Methylbenzyl)Amide: Application to the Asymmetric Synthesis of (R)-(-)-Angustureine.” Organic Letters, vol. 13, no. 10, 2011, pp. 2544–47.

Chicago Style

Bentley, SA, SG Davies, JA Lee, PM Roberts, and JE Thomson. 2011. “Conjugate Addition of Lithium N-Phenyl-N-(α-Methylbenzyl)Amide: Application to the Asymmetric Synthesis of (R)-(-)-Angustureine.” Organic Letters 13 (10): 2544–47.
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