Development of Chiral Spiro Phosphoramidites for Rhodium-Catalyzed Enantioselective Reactions

Chemistry : a European Journal
Zhiyao ZhengKuiling Ding

Abstract

A series of 1,1'-spirobiindane-7,7'-diol (SPINOL) analogues bearing a 2,2'-dimethyl-, cyclopentyl-, or cyclohexyl-fused ring were synthesized, and their distinct structural features were elucidated by X-ray crystallography. On the basis of these scaffolds, chiral monophosphoramidite ligands 6 a-m were synthesized, which demonstrated excellent enantioselectivity in RhI -catalyzed asymmetric hydrogenation of a dehydro amino acid methyl ester. Ligands 6 a-m were also successfully applied in the RhI -catalyzed enantioselective [4+2] cycloaddition of α,β-unsaturated imines with isocyanates, which afforded the corresponding pyrimidinones in good yields (60-92 %) with high enantioselectivities (75-92 % ee).

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Citations

Mar 29, 2020·Chemistry : a European Journal·Song YuTrevor A Hamlin
Mar 29, 2020·Organic Letters·Weicong GuoJun Wang

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