. Author manuscript; available in PMC: 2009 Dec 5.

Published in final edited form as: J Org Chem. 2008 Dec 5;73(23):9508–9510. doi: 10.1021/jo8020049

Table 1.

Conversion of •-methylstyrene to 6 using 1^(a)

Entry	Equiv	Reagent	Yield of 6	Ratio 6:7
1	1.5	1	30%^(b)	1.2:1
2	1.5	1	40%^(c)	1.1:1
3	1.5	1	31%^(d)	1.6:1
4	1.5	1	17%^(e)	5.2:1
5	2	1	60%	2.6:1
6	3	1	62%	3.8:1
7	6	1	80%	>10:1
8	10	1	82%	ND
9	1.5	2,6-lutidine-BH₂I	17%	1:2.9
10	2	Me₂SBH₂I	6%	1:5.6
11	2	Me₂SBH₃	19%	1:1.8

^(a)

HB in DCM at RT, 2 h, quenching at the indicated temperature with aqueous NaOH, followed by stirring with pinacol/NaOH, 15 h unless noted.

^(b)

average of three experiments (27-32%)

^(c)

HB, 18 h at 0 °C

^(d)

HB, 18 h at -20 °C

^(e)

HB, 18 h at -40 °C