Regio- and stereoselective allylindation of allenols regulated by a hydroxyl-chelated bicyclic transition state

Journal of the American Chemical Society

Volumn 118, Issue 19, 1996, Pages 4699-4700

  Araki, Shuki ^a   Usui, Hidenao ^a   Kato, Motoshi ^a   Butsugan, Yasuo ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029890653     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954318g     Document Type: Article

References (15)

1. For recent reviews on carbometalation, see: (a) Knochel, P. Carbometallation of Alkenes and Alkynes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 865-911. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38-52 (c) Norman, J. F.; Alexakis, A. Synthesis 1981, 841-870.
2. For recent reviews on carbometalation, see: (a) Knochel, P. Carbometallation of Alkenes and Alkynes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 865-911. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38-52 (c) Norman, J. F.; Alexakis, A. Synthesis 1981, 841-870.
3. For recent reviews on carbometalation, see: (a) Knochel, P. Carbometallation of Alkenes and Alkynes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 865-911. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38-52 (c) Norman, J. F.; Alexakis, A. Synthesis 1981, 841-870.
4. Examples of carbometalation of allenes. Allylzincation (allylcupration): Norman, J. F.; Quirion, J. Ch.; Masuda, Y.; Alexakis, A. Tetrahedron Lett. 1990, 31, 2879-2882. Norman, J. F.; Quirion, J. Ch.; Aiexakis, A.; Masuda, Y. Tetrahedron Lett. 1989, 30, 3955-3958. Norman, J. F.; Quirion, J. Ch Tetrahedron Lett. 1989, 30, 3959-3962 Allylmagnesiation: Richey, H. G., Jr.; Szucs, S. S. Tetrahedron Lett. 1971, 3785-3787. Allylboration: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505-523 and references cited therein.
5. Examples of carbometalation of allenes. Allylzincation (allylcupration): Norman, J. F.; Quirion, J. Ch.; Masuda, Y.; Alexakis, A. Tetrahedron Lett. 1990, 31, 2879-2882. Norman, J. F.; Quirion, J. Ch.; Aiexakis, A.; Masuda, Y. Tetrahedron Lett. 1989, 30, 3955-3958. Norman, J. F.; Quirion, J. Ch Tetrahedron Lett. 1989, 30, 3959-3962 Allylmagnesiation: Richey, H. G., Jr.; Szucs, S. S. Tetrahedron Lett. 1971, 3785-3787. Allylboration: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505-523 and references cited therein.
6. Examples of carbometalation of allenes. Allylzincation (allylcupration): Norman, J. F.; Quirion, J. Ch.; Masuda, Y.; Alexakis, A. Tetrahedron Lett. 1990, 31, 2879-2882. Norman, J. F.; Quirion, J. Ch.; Aiexakis, A.; Masuda, Y. Tetrahedron Lett. 1989, 30, 3955-3958. Norman, J. F.; Quirion, J. Ch Tetrahedron Lett. 1989, 30, 3959-3962 Allylmagnesiation: Richey, H. G., Jr.; Szucs, S. S. Tetrahedron Lett. 1971, 3785-3787. Allylboration: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505-523 and references cited therein.
7. Examples of carbometalation of allenes. Allylzincation (allylcupration): Norman, J. F.; Quirion, J. Ch.; Masuda, Y.; Alexakis, A. Tetrahedron Lett. 1990, 31, 2879-2882. Norman, J. F.; Quirion, J. Ch.; Aiexakis, A.; Masuda, Y. Tetrahedron Lett. 1989, 30, 3955-3958. Norman, J. F.; Quirion, J. Ch Tetrahedron Lett. 1989, 30, 3959-3962 Allylmagnesiation: Richey, H. G., Jr.; Szucs, S. S. Tetrahedron Lett. 1971, 3785-3787. Allylboration: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505-523 and references cited therein.
8. Examples of carbometalation of allenes. Allylzincation (allylcupration): Norman, J. F.; Quirion, J. Ch.; Masuda, Y.; Alexakis, A. Tetrahedron Lett. 1990, 31, 2879-2882. Norman, J. F.; Quirion, J. Ch.; Aiexakis, A.; Masuda, Y. Tetrahedron Lett. 1989, 30, 3955-3958. Norman, J. F.; Quirion, J. Ch Tetrahedron Lett. 1989, 30, 3959-3962 Allylmagnesiation: Richey, H. G., Jr.; Szucs, S. S. Tetrahedron Lett. 1971, 3785-3787. Allylboration: Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505-523 and references cited therein.
9. Araki, S.; Imai, A.; Shimizu, K.; Yamada, M.; Mori, A.; Butsugan, Y. J. Org. Chem. 1995, 60, 1841-1847.
10. 4). The solvent was removed, and the residue was distilled with a Kugelrohr apparatus (bath temperature: 105 °C/3 Torr) to give 5-phenyl-2,6-heptadien-1-ol (97%).
11. Fukuzawa, S.; Sakai, S. Bull. Chem. Soc. Jpn. 1992, 65, 3308-3314.
12. The importance of a free hydroxyl group was also demonstrated in indium-prompted allylation of α-hydroxy aldehydes: Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863-6866.
13. 3
14. Similarly, poor diastereoselectivity was observed in the allylation of carbonyl compounds with allylic indium sesquihalides: Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831-1833.
15. Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.-J.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538-2542.