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. Author manuscript; available in PMC: 2012 Sep 11.
Published in final edited form as: Science. 2012 Mar 22;336(6079):324–327. doi: 10.1126/science.1219274

Table 2.

Direct anti-diastereoselective and enantioselective carbonyl crotylation via hydrohydroxyalkylation of butadiene and related aldehyde-reductive couplings using the BINOL-derived phosphate counterion A9. Characterization methods were as described in Table 1.

graphic file with name nihms403825t3.jpg
Entry Product [o] Level Y [%] 4a (dr) er
1 graphic file with name nihms403825t4.jpg Alcohol
Aldehyde		 86 (8:1)
74 (8:1)		 95:5
94:6
2 graphic file with name nihms403825t5.jpg Alcohol
Aldehyde		 80 (7:1)
80 (6:1)		 94:6
93:7
3 graphic file with name nihms403825t6.jpg Alcohol
Aldehyde		 83 (7:1)
63 (6:1)		 96:4
94:6
4 graphic file with name nihms403825t7.jpg Alcohol
Aldehyde		 97 (5:1)
78 (5:1)		 93:7
93:7
5 graphic file with name nihms403825t8.jpg Alcohol
Aldehyde		 85 (6:1)
80 (5:1)		 93:7
94:6
6 graphic file with name nihms403825t9.jpg Alcohol
Aldehyde		 72 (6:1)
66 (6:1)		 93:7
94:6
7 graphic file with name nihms403825t10.jpg Alcohol
Aldehyde		 95 (9:1)
79 (4:1)		 94:6
93:7