Boronic Ester Homologation with 99% Chiral Selectivity and Its Use in Syntheses of the Insect Pheromones (3S,4S)-4-Methyl-3-heptanol and exo-Brevicomin

Journal of the American Chemical Society

Volumn 105, Issue 7, 1983, Pages 2077-2078

  Matteson, Donald S ^a   Sadhu, Kizhakethil M ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001275870     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00345a074     Document Type: Article

References (11)

1. (1) Matteson, D.S.; Ray, R. J. Am. Chem. Soc. 1980, 102, 7590-7591. Matteson, D.S.; Ray, R.; Rocks, R.R., manuscript in preparation.
2. Matteson, D.S.; Sadhu, K.M.; Lienhard, G.E. J. Am. Chem. Soc. 1981, 103, 5241-5242.
3. Matteson, D.S.; Majumdar, D. J. Am. Chem. Soc. 1980, 102, 7588-7590.
4. Matteson, D.S.; Jesthi, P.K., manuscript in preparation.
5. Matteson, D.S.; Erdik, E., manuscript in preparation.
6. (a) Pearce, G.T.; Grove, W.E.; Silverstein, R.M.; Peacock, J.W.; Cuthbert, R.A.; Lanier, G.N.; Simeone, J.B. J. Chem. Ecol. 1975, 1, 115. (b) Mori, K. Tetrahedron 1977, 33, 289-294. (c) Mori, K.; Iwasawa, H. Tetrahedron 1980, 36, 2209-2213.
7. Boronic acids are readily prepared from Grignard reagents: Washburn, R.M.; Levens, E.; Albright, C.F.; Billig, F.A. “Organic Syntheses'; Wiley: New York, 1963; Collect. Vol. IV, pp. 68-72. Esterification: ref 1 and 2. Hydroboration routes to boronic acids are of potential interest: Brown, H.C.; Jadhav, P.K.; Desai, M.C.J. Am. Chem. Soc. 1982, 104, 4303-4304.
8. Pinanediol: Ray, R.; Matteson, D.S. J. Indian Chem. Soc. 1982, 52, 119-123. Enantiomeric purification: ref 2.
9. Dale, J.A.; Dull, D.L.; Mosher, H.S. J. Org. Chem. 1969, 34, 2543-2549.
10. Racemic examples: (a) Bellas, T.E.; Brownlee, R.G.; Silverstein, R.M. Tetrahedron 1969, 25, 5149-5153. (b) Wasserman, H.H.; Barber, E.H.J. Am. Chem. Soc. 1969, 91, 3674-3675. (c) Hoffmann, R.W.; Kemper, B. Tetrahedron Lett. 1982, 23, 845-848. (d) Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4959-4962. (e) Wuts, P.G.M.; Bigelow, S.S. Synth. Commun. 1982, 12, 779-785.
11. Chiral syntheses: (a) Mori, K. Tetrahedron 1974, 30, 4223-4227. (b) Sherk, A.E.; Fraser-Reid, B.J. Org. Chem. 1982, 47, 932-935. (c) Johnston, B.D.; Oehlschlager, A.C.J. Org. Chem. 1982, 47, 5384-5386. (d) Masaki, Y.; Nagata, K.; Senzawa, Y.; Kaji, K. Tetrahedron Lett. 1982, 23, 5553-5554 and references cited therein.