Highly selective directed hydrogenation of enantiopure 4-(tert-butoxycarbonylamino) cyclopent-1-enecarboxylic acid methyl esters

…, MC Lloyd, SJC Taylor, DA Chaplin, R McCague

Index: Smith, Mark E.B.; Derrien, Nadine; Lloyd, Michael C.; Taylor, Stephen J.C.; Chaplin, David A.; McCague, Raymond Tetrahedron Letters, 2001 , vol. 42, # 7 p. 1347 - 1350

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Citation Number: 26

Abstract

The use of both N-tert-butoxycarbonylamino-and hydroxyl-directed hydrogenation methodology to yield essentially single diastereomers of 3-(tert-butoxycarbonylamino)-4- hydroxycyclopentanecarboxylic acid methyl esters and 3-(tert-butoxycarbonylamino) cyclopentanecarboxylic acid methyl esters is described. These results incorporate the first reported carbamate-directed hydrogenations of functionalised cyclopentenes.

Use of hydrolases for the synthesis of cyclic amino acids

[Lloyd, Richard C.; Lloyd, Michael C.; Smith, Mark E. B.; Holt, Karen E.; Swift, Jonathan P.; Keene, Philip A.; Taylor, Stephen J. C.; McCague, Raymond Tetrahedron, 2004 , vol. 60, # 3 p. 717 - 728]

An efficient route to all eight stereoisomers of a tri-funct...

[Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705]