Convenient preparation of carbonyl compounds from 1,2-diols utilizing Mitsunobu conditions

Tetrahedron Letters

Volumn 41, Issue 12, 2000, Pages 1959-1962

  Barrero, Alejandro F ^a   Alvarez Manzaneda, Enrique J ^a   Chahboun, R ^a  

^a Fac Ciencias   (Spain)

Author keywords

Aldehydes; Diols; Mitsunobu reactions

Indexed keywords

CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034681789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00071-X     Document Type: Article

References (18)

1. Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382.
2. Mitsunobu, O. Synthesis 1981, 1-28.
3. Camp, D.; Jenkins, I. A. Aust. J. Chem. 1988, 41, 1835-1840.
4. Manna, S.; Falck, J. R. Synth. Commun. 1985, 15, 663-665.
5. Edwards, M. L.; Stemerick, D. M.; McCarthy, J. R. Tetrahedron Lett. 1990, 31, 3417-3420.
6. Hoffman, W. A. J. Org. Chem. 1982, 47, 5209-5210.
7. Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin Jr., J. F. J. Am. Chem. Soc. 1980, 102, 7026-7032.
8. Kolasa, T.; Miller, M. J. J. Org. Chem. 1987, 52, 4978-4984.
9. Mitsunobu, O.; Keido, T.; Nishida, M. Chem. Lett. 1980, 1613-1615.
10. Guthrie, R. D.; Jenkins, I. D.; Yamasaki, R. J. Chem. Soc., Chem. Commun. 1980, 784-785.
11. Mitsunobu, O.; Kimura, J.; Inzuma, K.; Yanagida, N. Bull. Chem. Soc. Jpn. 1976, 49, 510-513.
12. Mengel, R.; Bartke, M. Angew. Chem., Int. Ed. Engl. 1978, 17, 697-780.
13. Kinoshita, M.; Taniguchi, M. Bull. Chem. Soc. Jpn. 1988, 61, 2147-2156.
14. Kimura, J.; Fujisawa, Y.; Sawada, T.; Mitsunobu, O. Chem. Lett. 1974, 691-692.
15. McGowan, D. A.; Berchtold, G. A. J. Org. Chem. 1981, 46, 2381-2383.
16. Razmilic, I.; Sierra, J. R.; Cortés, M. Chem. Lett. 1985, 1113.
17. Simmons, D. P.; Reichlin, D.; Skuy, D. Helv. Chim. Acta 1988, 71, 1000-1006.
18. 3): δ 0.03 (s, 3H, Me-Si), 0.04 (s, 3H, Me-Si), 0.83 (s, 3H, Me-13), 0.85 (s, 3H, Me-14), 0.87 (s, 9H, t-Bu-Si), 0.94 (dt, J=13.0, 3.9 Hz, 1H, H-1α), 1.04 (d, J=6.4 Hz, 3H, Me-12), 1.12 (m, 1H, H-9), 1.14 (s, 3H, Me-15), 1.17 (dd, J=13.5, 3.9 Hz, 1H, H-3α), 1.19 (d, J=3.8 Hz, H-5), 1.42 (bd, J=12.6 Hz, 1H, H-3β), 1.47 (dq, J=13.1 Hz, 1H, H-2α), 1.64 (dt, J=13.7, 10.4, 3.4 Hz, 1H, H-2β), 1.86 (bd, J=13.1 Hz, 1H, H-1β), 2.31 (d, J=13.9 Hz, 1H, H-6), 2.36 (dd, J=13.9, 3.8 Hz, 1H, H-6), 2.65 (dq, J=12.2, 6.4 Hz, 1H, H-8), 3.59 (dd, J=11.0, 4.1 Hz, 1H, H-11), 3.85 (dd, J=11.0, 1.7 Hz, 1H, H-11).