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. Author manuscript; available in PMC: 2014 Jan 9.
Published in final edited form as: J Am Chem Soc. 2012 Dec 26;135(1):82–85. doi: 10.1021/ja311061n

Table 1.

Enantioselective Homocrotylation Scopea

graphic file with name nihms431614u1.jpg
entry aldehyde time % y % eeb product/dr
1 graphic file with name nihms431614t1.jpg (11a) 14 h 83 97
2 n-hept-CHO (11b) 14 h 89 97
3 (C6H11)CHO (11c) 14 h 89 97
4 i-PrCHO (11d) 50 h 72 (83) 98
5 t-BuCHO (11e) 7 d 62 (84) 98
6 PhCH2CHO (11f) 14 h 82 97
7 graphic file with name nihms431614t2.jpg (11g) 14 h 89 97
8 graphic file with name nihms431614t3.jpg (11h) 48 h 83 graphic file with name nihms431614t4.jpg
>20:1 drd
9c graphic file with name nihms431614t5.jpg (11h)c 48 h 78 graphic file with name nihms431614t6.jpg
>20:1 drd
10 graphic file with name nihms431614t7.jpg (11i) 90 h 76 (87) graphic file with name nihms431614t8.jpg
>99:1d
11c graphic file with name nihms431614t9.jpg (11i)c 90 h 81 (96) graphic file with name nihms431614t10.jpg
>99:1d
a

3.0 equiv 1 and 1.5 equiv PhBCl2. Yields are isolated except where parentheses indicate NMR yields.

b

ee’s measured by chiral HPLC of alcohol or its benzoate derivative and are probably equal within error of measurement. Entries 1–7: no anti diastereomer was detected.

c

Ent-1 was used

d

Dr’s measured by RP HPLC or GC.