Unusual regioselectivity in the reductive coupling of alkynes and allenes by hydrozirconation and zinca-claisen rearrangement

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 22, 1997, Pages 2469-2471

  Suzuki, Keisuke ^a   Imai, Takahiro ^b   Yamanoi, Shigeo ^b   Chino, Masao ^b   Matsumoto, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031440509     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199724691     Document Type: Article

References (15)

1. a) M. Gaudemar, C. R. Acad. Sci. Paris (C) 1971, 273, 1669;
2. b) Y. Frangin, M. Gaudemar, ibid. 1974, 275, 885;
3. c) Synthesis 1977, 205;
4. d) P. Knochel, J.-F. Normant, Tetrahedron Lett. 1986, 27, 1039, 1043, 4427, 4431, 5727.
5. For a review of carbometalations see P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, Oxford, 1991, p. 865.
6. a) I. Marek, J.-M. Lefrançois, J.-F. Normant, J. Org. Chem. 1994, 59, 4154;
7. b) Bull. Soc. Chim. Fr. 1994, 131, 910.
8. 2 in Scheme 1) or the aggregation state of the dimetalated species. We wish to thank Dr. Ilane Marek for helpful discussions.
9. No additional zinc salt is required if at least one of the starting materials is an organozinc derivative.
10. For a review of allylmetal compounds see Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207.
11. J. Schwartz, J. A. Labinger, Angew. Chem. 1976, 88, 402; Angew. Chem. Int. Ed. Engl. 1976, 15, 333.
12. J. Schwartz, J. A. Labinger, Angew. Chem. 1976, 88, 402; Angew. Chem. Int. Ed. Engl. 1976, 15, 333.
13. Hydrozirconation of allenes: a) H. Maeta, T. Hasegawa, K. Suzuki, Synlett 1993, 341; b) K. Suzuki, T. Hasegawa, T. Imai, H. Maeta, S. Ohba, Tetrahedron 1995, 51, 4482; c) M. Chino, T. Matsumoto, K. Suzuki, Synlett 1994, 359.
14. Hydrozirconation of allenes: a) H. Maeta, T. Hasegawa, K. Suzuki, Synlett 1993, 341; b) K. Suzuki, T. Hasegawa, T. Imai, H. Maeta, S. Ohba, Tetrahedron 1995, 51, 4482; c) M. Chino, T. Matsumoto, K. Suzuki, Synlett 1994, 359.
15. Hydrozirconation of allenes: a) H. Maeta, T. Hasegawa, K. Suzuki, Synlett 1993, 341; b) K. Suzuki, T. Hasegawa, T. Imai, H. Maeta, S. Ohba, Tetrahedron 1995, 51, 4482; c) M. Chino, T. Matsumoto, K. Suzuki, Synlett 1994, 359.