Synthetic Application of Acyloin Condensation

Blanchard, A. N.; Burnell, D. J. Tetrahedron Lett. 2001, 42, 4779-4781.

 Synthetic Application of Acyloin Condensation

bis-silyloxyalkene formation

Blanchard, A. N.; Burnell, D. J. Tetrahedron Lett. 2001, 42, 4779-4781.

 bis-silyloxyalkene Formation

O Na O Na
O
OEt 2Na  OEt OEt
O O O O O O
OEt reduction OEt OEt
Na O
O Na O

Na
-2 OEt O 2Na  O
O O O O
reduction
O O
Na

TMSCl OTMS
O O

OTMS
 Bicyclic diketone Formation

Bicyclic diketone formation

Blanchard, A. N.; Burnell, D. J. Tetrahedron Lett. 2001, 42, 4779-4781.

 Bicyclic diketone Formation

O
OH
TMSO
OTMS O OH O O
O O
 Bicyclic diketone Formation

TMSO OTMS
OTMS BF3Et2O BF3 OTMS
O O O O

BF3 OTMS
O TMSO 1 OTMS
OTMS TFA O OTMS O 2
O 6 O
3 5 6
3 5
1 7
4
2 4

2
O
1 7
5
4 6
3

Shimada, J.; Hashimoto, K.; Kim, B. H.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 1759-
1773.