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. Author manuscript; available in PMC: 2012 Jun 15.
Published in final edited form as: Chem Sci. 2011 Sep 2;2(12):2378–2382. doi: 10.1039/C1SC00434D

Table 2.

Scope of the one-pot cyclopentane synthesis with alcohols 2.

graphic file with name nihms370293t2.jpg
entry comp. R yielda
(%)		 drb eec
(%)
1 a Me 95 > 20 : 1 82
2 b i-Pr 67 > 20 : 1 80
3 c i-Bu 73 > 20 : 1 80
4 d n-Hex 80 > 20 : 1 78
5 e graphic file with name nihms370293t3.jpg 86 > 20 : 1 76
6 f graphic file with name nihms370293t4.jpg 45d > 20 : 1 90 (96)e
7 g graphic file with name nihms370293t5.jpg 65f > 20 : 1 78
8 h Bn 42 > 20 : 1 87
9 i graphic file with name nihms370293t6.jpg 59 > 20 : 1 84
a

Isolated yield.

b

Determined from 1H NMR of crude reaction mixture.

c

Determined by chiral HPLC.

d

Yield of the deprotected ketone.

e

Number in parentheses indicates ee of recrystallized product.

f

Reaction conducted in refluxing heptane in the absence of Sc(OTf)3.