Bibliographic Details
| Title: |
P-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis. |
| Authors: |
Hsin Y. Su1, Taylor, Mark S.1 mtaylor@chem.utoronto.ca |
| Source: |
Journal of Organic Chemistry. 3/17/2017, Vol. 82 Issue 6, p3173-3182. 10p. |
| Abstract: |
The synthesis of stereodefined β-aminophosphines having both carbon- and phosphorus-based chirality centers is described. The method involves resolution of a mixture of β-aminophosphine oxide diastereomers accessed by ring-opening of an amino alcohol-derived cyclic sulfamidate. A stereospecific, borane-promoted reduction of β-aminophosphine oxides, which occurs under mild conditions and with inversion of configuration at phosphorus, is a key step in this process. The products obtained are new building blocks for the synthesis of P-chiral ligands and organocatalysts. In a proof-of-concept application in organocatalysis, the diastereomeric P-chiral β-aminophosphine-based bifunctional thioureas displayed significantly different activities in the Morita-Baylis-Hillman reaction of methyl acrylate with benzaldehyde derivatives. [ABSTRACT FROM AUTHOR] |
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| Database: |
Engineering Source |
