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. Author manuscript; available in PMC: 2012 Aug 17.
Published in final edited form as: J Am Chem Soc. 2011 Jul 27;133(32):12584–12589. doi: 10.1021/ja206013j

Table 1.

Intermolecular C—H Esterification with Homoallylic Oxygen Substitution

graphic file with name nihms314706u1.jpg
entry R R′a additive isolated yieldb L:Bc 3/4 E:Z (3)d dr (4)e
1 CH2CO2Me Ac none 11 1:2 >20:1 16:1
2 CH2CO2Me Ac Cr(salen)Cl 10 >20:1 >20:1 N/A
3 CH2CO2Me p-NO2Bz none 16 1:2 nd >20:1
4 CH2CO2Me p-NO2Bz Cr(salen)Cl >5 nd nd nd
5 Bn p-NO2Bz none >5 nd nd nd
a

AcOH (4.0 equiv) or p-NO2BzOH (1.5 equiv) used as the acid nucleophile.

b

Average of 2 runs at 0.5 mmol.

c

Linear(L):Branched(B) ratio determined by GC of the crude reaction after workup.

d

E:Z ratio determined by GC of the crude reaction after workup.

e

Diastereomeric ratio determined by GC of the crude reaction after workup. BQ = p-benzoquinone, salen = 1,2-cyclohexanediamine-N, N′-bis(3,5-di-tert-butylsalicylidine).