Development of Chiral Spiro Phosphoramidites for Rhodium-Catalyzed Enantioselective Reactions.
Chemistry
; 25(40): 9491-9497, 2019 Jul 17.
Article
em En
| MEDLINE
| ID: mdl-30817040
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,ß-unsaturated imines with isocyanates, which afforded the corresponding pyrimidinones in good yields (60-92 %) with high enantioselectivities (75-92 % ee).
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MEDLINE
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En
Ano de publicação:
2019
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Article