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New methodology for the synthesis of homochiral unsaturated amines

Rae, Alastair; (1998) New methodology for the synthesis of homochiral unsaturated amines. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

New methodology for the synthesis of chiral propargyl amines is described. A chiral (N)-Boc-l,3-amino alcohol, derived by the homologation of (L)- alanine with diazomethane, has been synthesised and this was then used, via reaction with a series of diethyl acetals, in the synthesis of chiral 1,3- tetrahydrooxazines (aminals). The structure of the aminals was determined, by both solution NMR and X- ray crystallographic methods, to exist as a twist chair structure with unusual conformational properties. The aminals were then functionalised with the Grignard reagent of (trimethylsilyl)acetylene, in the presence of boron trifluoride diethyl etherate, to give novel, ring opened, unsaturated amino alcohols. The subsequent unmasking of the required amines was then carried out by oxidation and subsequent retro-Michael elimination. The degree of chiral induction was determined via the Moshers amide method, and ranged from moderate to excellent.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: New methodology for the synthesis of homochiral unsaturated amines
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
Keywords: Pure sciences; Synthesis of homochiral unsaturated amines
URI: https://discovery.ucl.ac.uk/id/eprint/10103077
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