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Synthesis of Proline Derivatives of Bile Acids and Their Evaluation as Organocatalysts in the Asymmetric Direct Aldol Reaction by Gian Luigi Puleo; Matteo Masi; Anna Iuliano is a Chemistry article available to read on EtoBox.

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A new family of bile acid derived organocatalysts was obtained by linking L L-or D D-proline to amino derivatives of cholic and deoxycholic acids, which were used to promote the asymmetric direct aldol reaction between acetone and 4-nitrobenzaldehyde. Both the activity and enantioselectivity of the organocatalytic systems were dependent not only on the position of the proline moiety on the cholestanic backbone and its absolute configuration, but also on the presence of free hydroxyl group on the steroidal skeleton. The cholic acid derivative bearing a D D-prolinamide moiety at the 12-position and free hydroxyl groups at the 3-and 7-positions emerged as the best organocatalytic system giving complete conversion of the substrate, even when using only 2% of catalyst loading and ee up to 80%.

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Author

Gian Luigi Puleo; Matteo Masi; Anna Iuliano

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

2007

Language

EN

Field

Chemistry (Physical Sciences)