Catalytic asymmetric Simmons-Smith cyclopropanation of silyl enol ethers. Efficient synthesis of optically active cyclopropanol derivatives.
[reaction: see text] This paper describes a catalytic asymmetric Simmons-Smith cyclopropanation of silyl enol ethers using dipeptide 2 as the ligand. A variety of optically active cyclopropyl silyl ethers can be obtained in high yields. Up to 96% ee was obtained. The dipeptide can be recovered after the reaction in good yield and reused without the loss of reactivity or enantioselectivity.
Du
Haifeng
H
Department of Chemistry, Colorado State University, Fort Collins, 80523, USA.
Long
Jiang
J
Shi
Yian
Y
D002384:Catalysis; D004151:Dipeptides / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*
D004151:Dipeptides; D004987:Ethers; D004988:Ethers, Cyclic; D012821:Silanes; C043657:cyclopropanol