This document appears to be summarizing the results of an experiment testing different reaction conditions and substrates. It includes tables reporting yields, diastereoselectivity, and E:Z ratios for 10 different entries using various R1 and R2 groups. The tables also include results reported in brackets for comparison. Sections of text discuss the use of n-BuLi and t-BuOK in the reactions and 19F NMR characterization of products. Diagrams show structures of reactants and products involved in the transformations studied.

1. 2009
More Sense
More Sense

3. Contents
1

4. 2

5. 3

6. 4

7. 5

8. 6

9. 7

10. 8

11. 9

12. 10

13. 11

14. 12

15. 2,116 kw 39,231
915 P.19
195 Kl
P.14 16
8,184 l
13,733 l 13 t
LPG 596 238 t
P.16
INPUT
P.21 31 P.32 33
P.36 38
P.35 44
OUTPUT
239 t CO2
pH P.14
8.2
8.7
BOD 435 t
132 /l 71 t
189 /l 37 t
P.19 P.16 17
13

16. 14

17. 15

18. 16

19. 17

20. 18

21. 19

22. 20

23. 21

24. 22

25. 23

26. OAc OAc
AcO AcO
O O
AcO AcO
NHBoc
AcHN AcHN
O OBut
O O O(CH 2 )21CH3
O O O
H O H O O
H H
O N N N N N N O
N N N N N N
O H H H H H H
O O O O O O O(CH 2) 21 CH3
t
O OBu
NHBoc
24

27. 25

28. 26

29. 27

30. 28

31. Entry R1 R2 Yield of 1a) (%) Diastereoselectivitya) Yield of 3c) (%) E : Zc)
1 1-Naphthyl H 73 61:39 53 (64) <1:>99 (<1:>99)
2 Ph H 83 [83] 60:40 [51:49] 65 (72) <1:>99 (<1:>99)
3 p-MeO-C6H4- H 89 [82] 57:43 [51:49] 72 (72) <1:>99 (<1:>99)
4 p-Me-C6H4- H 90 [85] 59:41 [51:49] 89 (70) <1:>99 (<1:>99)
5 p-Br-C6H4- H 78 [64] 60:40 [51:49] trace (–) – (–)
6 p-F3C-C6H4- H 72 [33] 59:41 [56:44] trace (71) – (<1:>99)
7 C9H19- H 74 [–] 52:48 [–] trace (59) – (<1:>99)
8 PhCH2CH2- H 81 51:49 trace (80) – (<1:>99)
b) b)
9 (E)-PhCH=CH- H 82 [12] 56:44 [56:44] 26 (31) 13:87 (<1:>99)
10 Ph Me 85 40:60 87 (70) 38:62 (27:73)
a) BuLi t-BuOK
19
b) F NMR c [3,3]
29

32. 30

33. 31

34. 32

35. 33

36. 34

37. 35

38. 36

39. 37

40. 38

41. 39

42. 40

43. 41

44. 42

45. 43

46. 44

47. 45

48. 46