Skip to main content
. Author manuscript; available in PMC: 2008 Nov 21.
Published in final edited form as: Organometallics. 2006 Nov;25(19):4621–4626. doi: 10.1021/om060430j

Table 4.

Generation of binaphtholate catalysts in situ and conversions (ee) for asymmetric ring closing metathesis (equation 5).

time (h), temp (°C) % amide conv (% catalyst) % substrate conv (% ee)
H2[R-Benz2Bitet] graphic file with name nihms61235t1.jpg R″ = Ar 8.0, 50 100(81) 77(94)a
R″ = Ar′ 1.0, 70 100(100) 99(97)
H2[R-TRIP2BINO] graphic file with name nihms61235t2.jpg R″ = Ar 48.0, 60 100(100) 82(95)
R″ = Ar′ 48.0, 60 100(100) 99(96)
H2[R-Ph2BINO] graphic file with name nihms61235t3.jpg R″ = Ar 0.5, 50 100(100) 90(68)b
R″ = Ar′ 1.0, 70 100(100) 95(87)
H2[rac-Mes2BINO] graphic file with name nihms61235t4.jpg R″ = Ar 14.0, 70 100(100) 75c
R″ = Ar′ 14.0, 70 91(86) 93
H2[R-TMS2BINO] graphic file with name nihms61235t5.jpg R″ = Ar 8.0, 50 82(56) 92(72)
R″ = Ar′ 36.0, 70 90(90) 99(56)
a

With isolated catalyst22 95% conversion, 93% ee.

b

With isolated catalyst20 90% conversion, 75% ee.

c

With isolated enantiomerically pure catalyst20 92% conversion, 86% ee.