Denmark: Studies of Zn(CH2Ci)2 and zn(CH2)2 Zn(CH2X)2(2 equiv) DCE Substrate Yield x= cl de x= CI (=D 2 ICH2Cl Et2Zn Zn(CH2 CI)2 100(85) H2)2Zn reactions in benzene were plagued by rous side products resulting from reaction with 89(41) 99(995) (>99.5) 100(70) 82(91) Denmark, S; Edwards, J.J. Org. Chem. 1991, 56, 6974 Charette: Selective Cyclopropanation Conditions ICH2X (equiv) (equiv nt syn: anti (4) 9:1 2 X=1(4) toluene CH2x solvent X=1(10) X=C|(2) toluene X=1(4) toluene(0.35M)1:>25 toluene(0.05M) Zn(CH2I2.DME(2 toluene >25:1 Charette, A; Marcoux, J. Synlett, 1995, 1197 09B063/299812:25PMPh CH3 Ph O O OH OBn Ph O O na 100 (70) CO2i-Pr 99 (>99.5) CO2i-Pr 78 (> 99.5) 94 (12) 92 (88) 100 (85) 89 (41) 64 (98) Denmark: Studies of Zn(CH2Cl)2 and Zn(CH2I)2 + Zn(CH2X)2 (2 equiv) 82 (91) na na Substrate Yield X = Cl (X = I) d.e. X = Cl (X = I) • (ClCH2)2Zn reactions in benzene were plagued by numerous side products resulting from reaction with solvent Denmark, S.; Edwards, J. J. Org. Chem. 1991, 56, 6974 2 ICH2Cl + Et2Zn Zn(CH2Cl)2 2 CH2I2 + Et2Zn Zn(CH2I)2 DCE OBn OBn OBn 2 OH OBn >99 :1 OH 9 : 1 OH 1 : 1 OBn OBn syn:anti syn:anti Charette, A.; Marcoux, J. Synlett, 1995, 1197 Charette: Selective Cyclopropanation Conditions Syn Anti Et2Zn (equiv) ICH2X (equiv) solvent X = I (4) ClCH2CH2Cl 2 X = Cl (4) " 2 X = I (4) toluene Et2Zn (equiv) ICH2X (equiv) solvent 10 X = I (10) toluene 1 : >25 2 X = Cl (2) toluene 6 : 1 2 X = Cl (4) ClCH2CH2Cl 1 : >25 2 X = I (4) 2 X = I (4) Zn(CH2I)2•DME (2 equiv) toluene (0.35M) toluene (0.05M) toluene 1 : >25 1 : 2 >25 : 1 09B-06 3/29/98 12:25 PM