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. Author manuscript; available in PMC: 2010 Dec 30.
Published in final edited form as: J Am Chem Soc. 2009 Dec 30;131(51):18343–18357. doi: 10.1021/ja9053948

Table 4.

Reaction of Various Allyl Enol Carbonatesa

entry substrate product yieldb
eec
Lit,d
yield,
ee
1 graphic file with name nihms-161072-t0040.jpg graphic file with name nihms-161072-t0041.jpg 88%
99.7% ee
R-(+) e
99%
88% ee
R-(+)
2 graphic file with name nihms-161072-t0042.jpg graphic file with name nihms-161072-t0043.jpg 94%
91% ee f
(−)
90%
6% ee
(+)
3 graphic file with name nihms-161072-t0044.jpg graphic file with name nihms-161072-t0045.jpg 98%
76%ee
(+)
79%
38% ee
(+)
4 graphic file with name nihms-161072-t0046.jpg graphic file with name nihms-161072-t0047.jpg 64%
82% ee
(+)
59%
45% ee
(−)
5 graphic file with name nihms-161072-t0048.jpg graphic file with name nihms-161072-t0049.jpg 99%
95% ee
(+)
98%
82% ee
(−)
a

All reactions were performed on a 0.3 mmol scale at 0.1 M in toluene at 23 °C for 20 h using 2.5 mol% 20 and 5.5 mol% ligand (R,R)-L4.

b

Isolated yields.

c

Ee values were determined by HPLC on a chiral stationary phase.

d

Conditions used were 2.5 mol% [(η3-C3H5)PdCl]2, 5.0 mol% (S,S)-L1, 2.0 equiv LDA, 1.0 equiv Me3SnCl, DME, r.t.10

e

The absolute configuration and the sign of the optical rotation ([α]D) of the product.9a

f

Ee was determined by GC on a chiral stationary phase.