Facile one-pot procedure for Et3Al-promoted asymmetric pinacol-type rearrangement

Synthesis

Volumn , Issue 1, 2003, Pages 141-146

  Shionhara, Tomoichi ^a   Suzuki, Keisuke ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Diols; Lewis acids; Rearrangements; Triethylaluminum; chiral ketone

Indexed keywords

AROMATIC HYDROCARBONS; KETONES; SULFONATION;

ONE-POT PROCEDURE;

SYNTHESIS (CHEMICAL);

LEWIS ACID;

ANALYTIC METHOD; ASYMMETRIC SYNTHESIS; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PINACOL REARRANGEMENT; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STEREOSPECIFICITY; STOICHIOMETRY; SYNTHESIS;

EID: 0037242008     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-36266     Document Type: Review

References (12)

1. (a) Suzuki, K.; Katayama, E.; Tsuchihashi, G. Tetrahedron Lett. 1983, 24, 4997.
2. (b) Suzuki, K.; Katayama, E.; Tsuchihashi, G. Tetrahedron Lett. 1984, 25, 1817.
3. (a) Tsuchihashi, G.; Tomooka, K.; Suzuki, K. Tetrahedron Lett. 1984, 25, 4253.
4. (b) Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861.
5. (c) Suzuki, K.; Tomooka, K.; Katayama, E.; Matsumoto, T.; Tsuchihashi, G. J. Am. Chem. Soc. 1986, 108, 5221.
6. King, J. F.; Lee, T. W. S. J. Am. Chem. Soc. 1969, 91, 6524.
7. Shinohara, T.; Suzuki, K. Tetrahedron Lett. 2002, 43, 6937.
8. 1a was prepared by the reaction of (S)-ethyl lactate with phenyllithium at -78°C as shown in Scheme 4.
9. D value reported in ref 1a.
10. 1a followed by removal of the ethoxyethyl group as shown in Scheme 3.
11. Diols 1b-h were also prepared in a similar manner shown in Scheme 3.
12. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.