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Methyl 4-(N-benzyl-N-allylamino)but-2-enoate 4 can be prepared readily on a multigram scale by addition of N-benzyl-N-allylamine to methyl 4-bromocrotonate
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1H NMR spectroscopic analysis of the crude reaction product The absolute configuration of 5 was assigned as (3R,αS) by analogy with previous models developed to explain the stereoselectivity observed during addition of lithium amide 3 to α,β-unsaturated acceptors; see
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1H NMR spectroscopic analysis of the crude reaction product
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24
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33751183730
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1H NMR studies of the corresponding Mosher's amides of pyrrolidinone 17, obtained in 89% yield via hydrogenolysis of 6, and comparison with an authentic racemic standard.
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note
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(R)-(+)-3-Aminopyrrolidine (> 98% e.e.) is commercially available from Aldrich
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26
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33745190370
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Chemical Crystallography Laboratory, Oxford, UK For the established anti-alkylation preference of β-amino enolates see
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