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. Author manuscript; available in PMC: 2010 Mar 16.
Published in final edited form as: Tetrahedron Asymmetry. 2009 Jan 30;20(1):1–63. doi: 10.1016/j.tetasy.2009.01.002

Table 6.

Asymmetric cyclopropanation of styrene with α-nitro-α-diazocarbonyl compounds 361a–d.

graphic file with name nihms166053t11.jpg
Substrate Catalyst Aditive Yield
(%)		 Ratio
(trans:cis)		 % ee
(trans)		 % ee
(cis)
361a; R = OMe 362 -- 75 86 : 14 28 13
361b; R = OEt 362 -- 72 83 : 17 30 0
361c; R = Ot-Bu 362 -- 68 68 : 32 41 6
361d; R = Ph 362 -- 64 39 : 61 31 13
361b; R = OEt 363 -- 71 75 : 25 13 16
361b; R = OEt 364 -- 76 86 : 14 33 0
361b; R = OEt 365a -- 89 89 : 11 2 17
361b; R = OEt 365b -- 74 79 : 21 8 10
361a; R = OMea 366a (BzO)2 27 90 : 10 nd nd
361a; R = OMea 366a EDA (20%) 55 90 : 10 72 51
361a; R = OMea 366a EDA (10%) 52 90 : 10 66 49
361a; R = OMeb 366a PhNHNH2 39 90 : 10 70 49
361a; R = OMea 366b EDA (10%) 16 95 : 05 68 nd
361a; R = OMea 366c EDA (10%) 7 95 : 05 63 nd
a

in the presence of 5 mol% of Cu(MeCN)4PF6.

b

Cu(II)OTf2 was used as the copper source