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Synthesis of new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzed asymmetric hydrogenation reactions.
Org Lett. 2004 Sep 30; 6(20):3565-7.OL

Abstract

[reaction: see text] A new spirocyclic diol, 9,9'-spirobixanthene-1,1'-diol, was synthesized in two steps from readily available starting material m-phenoxyanisole. Resolution of the racemic diol was achieved by cocrystallization with N-benzylcinchonidinium chloride and N-benzylquininium chloride in acetonitrile. The corresponding spiro monodentate phosphoramidite ligand has been prepared for Rh-catalyzed asymmetric hydrogenation of alpha-dehydroamino acid derivatives and itaconic acid with excellent enantioselectivities (up to >99% ee).

Authors+Show Affiliations

Department of Chemistry, 104 Chemistry Research Building, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15387549

Citation

Wu, Shulin, et al. "Synthesis of New Monodentate Spiro Phosphoramidite Ligand and Its Application in Rh-catalyzed Asymmetric Hydrogenation Reactions." Organic Letters, vol. 6, no. 20, 2004, pp. 3565-7.
Wu S, Zhang W, Zhang Z, et al. Synthesis of new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzed asymmetric hydrogenation reactions. Org Lett. 2004;6(20):3565-7.
Wu, S., Zhang, W., Zhang, Z., & Zhang, X. (2004). Synthesis of new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzed asymmetric hydrogenation reactions. Organic Letters, 6(20), 3565-7.
Wu S, et al. Synthesis of New Monodentate Spiro Phosphoramidite Ligand and Its Application in Rh-catalyzed Asymmetric Hydrogenation Reactions. Org Lett. 2004 Sep 30;6(20):3565-7. PubMed PMID: 15387549.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzed asymmetric hydrogenation reactions. AU - Wu,Shulin, AU - Zhang,Weicheng, AU - Zhang,Zhaoguo, AU - Zhang,Xumu, PY - 2004/9/25/pubmed PY - 2005/11/1/medline PY - 2004/9/25/entrez SP - 3565 EP - 7 JF - Organic letters JO - Org Lett VL - 6 IS - 20 N2 - [reaction: see text] A new spirocyclic diol, 9,9'-spirobixanthene-1,1'-diol, was synthesized in two steps from readily available starting material m-phenoxyanisole. Resolution of the racemic diol was achieved by cocrystallization with N-benzylcinchonidinium chloride and N-benzylquininium chloride in acetonitrile. The corresponding spiro monodentate phosphoramidite ligand has been prepared for Rh-catalyzed asymmetric hydrogenation of alpha-dehydroamino acid derivatives and itaconic acid with excellent enantioselectivities (up to >99% ee). SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15387549/Synthesis_of_new_monodentate_spiro_phosphoramidite_ligand_and_its_application_in_Rh_catalyzed_asymmetric_hydrogenation_reactions_ L2 - https://doi.org/10.1021/ol048528m DB - PRIME DP - Unbound Medicine ER -