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Volumn 130, Issue 14, 2008, Pages 4897-4905

Organocatalytic asymmetric conjugate addition to allenic esters and ketones

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; AMMONIUM COMPOUNDS; DERIVATIVES; ENANTIOSELECTIVITY; KETONES; SUBSTITUTION REACTIONS;

EID: 41849101500     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710689c     Document Type: Article
Times cited : (91)

References (98)
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    • The crystallographic coordinates of 4g (CCDC 654132) as well as 10a (CCDC 664412) have been deposited with the Cambridge Crystallographic Data Centre
    • The crystallographic coordinates of 4g (CCDC 654132) as well as 10a (CCDC 664412) have been deposited with the Cambridge Crystallographic Data Centre. These data can be obtained free of charge from the the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • These data can be obtained free of charge from the the Cambridge Crystallographic Data Centre via
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    • This model was developed on the basis of an X-ray analysis of catalyst 6 bearing p-nitrophenolate as the counterion. See ref 21i
    • This model was developed on the basis of an X-ray analysis of catalyst 6 bearing p-nitrophenolate as the counterion. See ref 21i.
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    • It should be noted that 6 and 6′ are less effective catalysts compared to 8, giving the catalytic product in very low yield. In the solid state a p-nitrophenolate counterion in catalyst 6 was found to be in a different position with respect to the quaternary nitrogen atom, compared to the same counterion in catalyst 8, presumably due to the steric effects exerted by the 1-adamantoyl substituent. For a discussion, see ref 21i
    • It should be noted that 6 and 6′ are less effective catalysts compared to 8, giving the catalytic product in very low yield. In the solid state a p-nitrophenolate counterion in catalyst 6 was found to be in a different position with respect to the quaternary nitrogen atom, compared to the same counterion in catalyst 8, presumably due to the steric effects exerted by the 1-adamantoyl substituent. For a discussion, see ref 21i.
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    • It has to be noted that the more bulky glycine imine 2b has an opposite effect on the enantioselectivity with catalyst 8 giving the product 5b with only 35% ee.
    • It has to be noted that the more bulky glycine imine 2b has an opposite effect on the enantioselectivity with catalyst 8 giving the product 5b with only 35% ee.


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