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. Author manuscript; available in PMC: 2016 Apr 29.
Published in final edited form as: J Am Chem Soc. 2015 Apr 21;137(16):5292–5295. doi: 10.1021/jacs.5b01899

Table 1. Effect of Organophosphorus Catalyst on Regioselectivity of Transpositive Allylic Reductiona.

graphic file with name nihms-750780-t0011.jpg

entry R3Pb yieldc ratioc (4:5)
1 none 80  9:91
2 6 78 18:82
3 7 85 11:89
4 8 95 19:81
5 9 95 54:46
6 10 96 94:6
7 10 d 100 98:2
8 10 e 81 88:12
9 11 96 91:9
a

See Supporting Information for full experimental details.

b

See ref 17.

c

The combined yield and ratio of 4 and 5 were determined by GC analysis (dodecane internal standard).

d

Neutral trivalent 10 as catalyst.

e

10·HBF4 salt as precatalyst.