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. Author manuscript; available in PMC: 2011 Feb 17.
Published in final edited form as: J Am Chem Soc. 2010 Feb 17;132(6):1740–1741. doi: 10.1021/ja908257x

Table 1.

Catalyzed hydroborations of (E)- and (Z)-1 as a function of ligand 3a–d.a

Entry Ligand (E)-1 ee yield (Z)-1 ee yield
1 (BINOL)PN(Me)Ph 90 55 89 50
2 3a 89 65 90 81
3 3b 91 72 87 76
4 3c 98 79 96 80
5 3d 91 76 95 80
6b 3a 87 66
7c 3a 5 35
a

Unless otherwise specified, the reaction was run as follows: 1.0% Rh(nbd)2BF4, 2.1% of the indicated ligand, 2.0 PinBH, 40 °C, 12–24 h.

b

Uses 1.0% Rh(cod)2BF4.

c

Uses 0.5% [Rh(cod)Cl]2.