Benzylation of carboxylic acids by oxidation-reduction condensation using quinones and benzyloxydiphenylphosphine

Chemistry Letters

Volumn , Issue 11, 2002, Pages 1126-1127

  Mukaiyama, Teruaki ^a   Shintou, Taichi ^a   Kikuchi, Wataru ^a  

^a KITASATO INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLOXYDIPHENYLPHOSPHINE; CARBOXYLIC ACID DERIVATIVE; PHOSPHINE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; CHEMICAL REACTION; MITSUNOBU REACTION; OXIDATION REDUCTION REACTION; POLYMERIZATION; REACTION ANALYSIS;

EID: 0037027702     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.1126     Document Type: Article

References (13)

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3. T. Mukaiyama, R. Matsueda, and M. Suzuki, Tetrahedron Lett., 22, 1901 (1970).
4. O. Mitsunobu, M. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 40, 935 (1967).
5. a) O. Mitsunobu and M. Yamada, Bull. Chem. Soc. Jpn., 40, 2380 (1967).
6. b) O. Mitsunobu and M. Eguchi, Bull. Chem. Soc. Jpn., 44, 3427 (1971).
7. c) O. Mitsunobu, Synthesis, 1981, 1.
8. d) D. L. Hughs, in "Organic Reactions," ed. by P. Beak, et al., John Wiley & Sons, New York (1992), Vol. 42, p 335.
9. a) T. Tsunoda, F. Ozaki, and S. Ito, Tetrahedron Lett., 35, 5081 (1994).
10. b) S. Ito, Yakugaku Zasshi, 121, 567 (2001).
11. The equimolar amounts of chlorodiphenylphosphine and benzyl alcohol were mixed with the equimolar amounts of pyridine in diethyl ether at room temperature under argon atmosphere. Distillation gave colorless oil, Yield 55% (bp. 155-157°C/0.2 mmHg). See: B. A. Arbouzov and N. P. Grechkin, Zh. Obshch. Khim., 20, 107 (1950).
12. tR = 9.6min (D-valine derivative). N-tert-butoxycarbonyl-D-valine afforded the corresponding benzyl ester in 89% yield and no epimerization took place.
13. The reaction of benzoic acid with 1.1 equivalent of benzyl alcohol and triphenylphosphine was tried by using 1.0 equivalent of BDMQ in dichloromethane at room temperature, but the desired product was not obtained.