5(N-methylbenzoylamino)-2,2,6,6-tetramethylheptan-3-ol as a new class of recoverable chiral auxiliary

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1863-1866

  Yamamoto, Yoshinori ^a   Kin, Hirofumi ^a   Suzuki, Ichiro ^a   Asao, Naoki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYACID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029993774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00137-2     Document Type: Article

References (13)

1. Suzuki, I.; Kin, H.; Yamamoto, Y. J. Am. Chem. Soc. 1993, 115, 10139-10146.
2. Kadota, I.; Kobayashi, K.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun.. 1995, 1271-1272.
3. Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410-416. G. A. Lee, Synthesis. 1982, 508-509.
4. Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410-416. G. A. Lee, Synthesis. 1982, 508-509.
5. Müller, I.; Jäger, V. Tetrahedron Lett. 1982, 46, 4777-4780. Jäger, V.; Schwab, W.; Buβ, V. Angew. Chem. Int. Ed. Engl. 1981, 20, 601-603. The anti amino alcohol was not obtained at all.
6. Müller, I.; Jäger, V. Tetrahedron Lett. 1982, 46, 4777-4780. Jäger, V.; Schwab, W.; Buβ, V. Angew. Chem. Int. Ed. Engl. 1981, 20, 601-603. The anti amino alcohol was not obtained at all.
7. Selective benzoylation at an amino group took place under the reaction conditions. No benzoylation occurred at all at an alcohol group.
8. Brown, W. G. Org. React. 1951, 6, 469-509. Wilson, C. V.; Steinberg, J. F. Org. Synth, Coll. 1963, Vol IV, 564-565.
9. Brown, W. G. Org. React. 1951, 6, 469-509. Wilson, C. V.; Steinberg, J. F. Org. Synth, Coll. 1963, Vol IV, 564-565.
10. Doolittle, R. E.; Heath, R. R. J. Org. Chem. 1984, 49, 5041-5050.
11. Dhaon, M. K.; Olsen, R. K.; Ramasamy, K. J. Org. Chem. 1982, 47,. 1962-1965; Niwa, H.; Ogawa, T.; Yamada, K. Tetrahedron Lett. 1989, 30, 4985-4986.
12. Dhaon, M. K.; Olsen, R. K.; Ramasamy, K. J. Org. Chem. 1982, 47,. 1962-1965; Niwa, H.; Ogawa, T.; Yamada, K. Tetrahedron Lett. 1989, 30, 4985-4986.
13. Resolution using other chiral reagents such as α-methoxyacetyl chloride and (R)-2-phenylpropionic acid resulted in failure.