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. 2014 Nov 19;136(51):17738–17749. doi: 10.1021/ja510573v

Table 3. Lactamide and Mandelamide as Chiral Auxiliaries .

graphic file with name ja-2014-10573v_0021.jpg

entry starting material catalyst solvent yield 1 (%)a yield 2 (%)b ee %e
1 22a Rh2(S-PTAD)4 CH2Cl2 <10    
2 22a Rh2(R-PTAD)4 CH2Cl2 <10    
3 22a Rh2(S-DOSP)4 CH2Cl2 63 83 62
4 22a Rh2(R-DOSP)4 CH2Cl2 74 86 70
5 22a Rh2(OAc)4 CH2Cl2 84 84 65
6 22a Rh2(O2CC4F9)4 CH2Cl2 0    
7 22a Rh2(R-DOSP)4 (CH2Cl)2 72    
8 22a Rh2(R-DOSP)4 PhMe 61    
9 22a Rh2(R-DOSP)4 c-C6H12 <10    
10 22a Rh2(R-DOSP)4 CH3CN 0    
11 23b Rh2(S-DOSP)4 CH2Cl2 84 89 59
12 23b Rh2(R-DOSP)4 CH2Cl2 57 77 52
13 23b Rh2(OAc)4 CH2Cl2 72 85c 76
14 23b Rh2(OAc)4 CH2Cl2 61d 84 84
a

Isolated yield.

b

Combined isolated yield.

c

Isolated yield, complete isomerization to the trans isomer observed.

d

Major diastereomer isolated in pure form by column chromatography.

e

Determined by HPLC.