First example of highly stereoselective synthesis of 1,2,3-trisubstituted cyclopropanes via chiral selenonium ylides.
As the first example of the application of chiral selenonium ylides in asymmetric cyclopropanation, a new strategy for the highly stereoselective synthesis of chiral 1,2,3-trisubstituted cyclopropanes via selenonium ylides is described. The reaction afforded three stereoisomers of chiral 1,2,3-trisubstituted cyclopropanes with good yields, excellent diastereoselectivities, very high enantioselectivities (up to >99% ee), good generality and recyclability of chiral selenides. The possible pathways and models of the asymmetric cyclopropanation via the chiral selenonium ylides were also proposed to rationalize the excellent enantioselectivities and diastereoselectivities.
Wang
Hai-Yang
HY
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
Yang
Fei
F
Li
Xin-Liang
XL
Yan
Xue-Ming
XM
Huang
Zhi-Zhen
ZZ
D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D003521:Cyclopropanes; D016566:Organoselenium Compounds