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. Author manuscript; available in PMC: 2012 Dec 19.
Published in final edited form as: European J Org Chem. 2009 Oct 8;2009(32):5487–5500. doi: 10.1002/ejoc.200900560

Table 1.

Cuprate addition/phosphate acid cleavage sequence.

graphic file with name nihms425058t1.jpg
Entry (R1)2Zn or
R1ZnBr		 Phosphate acid - 11
yield (dr)		 Homoallylic
alcohol - 12		 % Yield
1 Me2Zn[a] 99% (20:1)
11a 		graphic file with name nihms425058t2.jpg 83
2 Et2Zn[a] 99%(>20:1)
11b 		graphic file with name nihms425058t3.jpg 90
3 iPr2Zn[a] 99%(>20:1)
11c 		graphic file with name nihms425058t4.jpg 95
4 cHexZnl[b] 99% (>20:1)
11d 		graphic file with name nihms425058t5.jpg 70
5 BnZnBr[b] 99% (>20:1)
11e 		graphic file with name nihms425058t6.jpg 84
6 CN(CH2)3ZnBr[b] 99% (>20:1)
11f 		graphic file with name nihms425058t7.jpg 31
7 Cl(CH2)4ZnBr[b] 99% (>20:1)
11g 		graphic file with name nihms425058t8.jpg 71
8 CH2=CH(CH2)3ZnBr[b] 99% (>20:1)
11h 		graphic file with name nihms425058t9.jpg 65
[a]

Method required 4–5 equiv. of organocuprate.

[b]

Method required 8–9 equiv. of organocuprate.