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A P∗-chiral bisdiamidophosphite ligand with a 1,4:3,6-dianhydro-d-mannite backbone and its application in asymmetric catalysis

✍ Scribed by Konstantin N. Gavrilov; Sergey V. Zheglov; Pavel A. Vologzhanin; Marina G. Maksimova; Anton S. Safronov; Sergey E. Lyubimov; Vadim A. Davankov; Benjamin Schäffner; Armin Börner

Book ID: 104095208
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 117 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.03.042

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✦ Synopsis

A novel readily available P,P-bidentate diamidophosphite ligand with P * -stereocentres is prepared from an inexpensive C 2 -symmetric 1,4:3,6-dianhydro-D-mannite. By using this efficient ligand, up to 98% ee is achieved in Pd-catalysed asymmetric allylic alkylation, up to 92% ee in Pd-catalysed asymmetric allylic amination and up to 87% ee in Rh-catalysed asymmetric hydrogenation. The influence of the precatalyst, substrate and solvent on the enantioselectivity is discussed.

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