Theoretical Investigation on the Role of Amine Bases in Stabilizing the Key Intermediate of Proline Enamine Carboxylate in Proline-Catalyzed Asymmetric Reactions
2014 ◽
Vol 998-999
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pp. 124-127
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Keyword(s):
Quantum mechanical calculations have been performed to study the equilibrium among the key intermediates (iminium ion, oxazolidione, and enamine) in the proline-catalyzed reactions under base-free and base-present conditions. The results confirmed that the tautomeric equilibrium among these species can be tuned by the basic additives. The computations satisfactorily rationalized the experimental observations and provide a clue on how to stabilize the enamine intermediates.
2015 ◽
Vol 17
(5)
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pp. 2917-2934
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1998 ◽
Vol 70
(2)
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pp. 331-339
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Keyword(s):
2008 ◽
Vol 112
(4)
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pp. 1293-1298
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2000 ◽
Vol 72
(12)
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pp. 2319-2332
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1979 ◽
Vol 16
(1)
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pp. 71-77
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2010 ◽
Vol 132
(47)
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pp. 16862-16872
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