Nucleophilic ring closure and opening of aminoiodohydrins

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1231-1234

  Concellón, José M ^a   Bernad, Pablo L ^a   Pérez Andrés, Juan A ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Azetidines; Epoxides; Halohydrines; Oxazolidines

Indexed keywords

AMINOALDEHYDE; AZETIDINE DERIVATIVE; EPOXIDE; IODINE DERIVATIVE; OXAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034685261     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02250-9     Document Type: Article

References (17)

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3. Midland, M. M.; Alfonso, M. M. J. Am. Chem. Soc. 1989, 111, 4368-4371.
4. Reetz, M. T.; Röhring, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1706-1709.
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6. Concellón, J. M.; Bernad, P. L.; Pérez-Andrés, J. A. J. Org. Chem. 1997, 62, 8902-8906.
7. Gaertner, V. R. J. Org. Chem. 1968, 33, 523-530.
8. Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1997, 62, 5974-5977.
9. The ratio of closure product to 3-amino-1-haloalkan-2-ols and derivatives is very dependent on the substitution pattern in the structure. For example, we have described that the iodohydrins 2 can be stabilised by acetylation of the alcohol group (Ref. 6). Substitution on the amine group or at C2 can also be an important effect. See: Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1995, 60, 6696-6699 and Ref. 8.
10. Chiral aminoepoxides are highly useful intermediates in the synthesis of protease inhibitors and other pharmaceutically interesting compounds. See, for example: Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487-1492.
11. For some applications of the allylic alcohols, see: (a) Reich, H. J.; Wollowitz, S. J. Am. Chem. Soc. 1982, 104, 7051-7059. (b) Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096-1104.
12. For some applications of the allylic alcohols, see: (a) Reich, H. J.; Wollowitz, S. J. Am. Chem. Soc. 1982, 104, 7051-7059. (b) Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096-1104.
13. Although thermodynamic control could be assumed, an anti elimination in the most stable conformer could not be counted upon.
14. Chiral HPLC analysis (Chiralcel OD-H) was carried out using, for comparison, a racemic mixture of the corresponding compound, to exclude the possibility of co-elution of both enantiomers. Aminoalcohol 6 could not be resolved using the chiral column Chiralcel OD-H; HPLC analysis was carried out with the corresponding benzoic ester, prepared by reaction of 6 with benzoyl chloride.
15. 2 as an alkylating agent, see: Spillane, W. J.; Burke, P. O. Synthesis 1986, 1021-1024.
16. Oxazolidines have been extensively used as intermediates in the synthesis of several compounds with biological activity: Marshall, J. A.; Beaudoin, S. J. Org. Chem. 1996, 61, 581-586.
17. 2, easily removed and purified by distillation.