Highly 1,2-trans stereoselective allylations of 1,2-O-isopropylidene-protected glycofuranosides

Angewandte Chemie - International Edition

Volumn 39, Issue 15, 2000, Pages 2727-2729

  García Tellado, Fernando ^a   De Armas, Pedro ^a   Marrero Tellado, José Juan ^b  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

Asymmetric synthesis; C C coupling; Carbohydrates; Glycosides; Lewis acids

Indexed keywords

GLYCOSIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0039592871     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000804)39:15<2727::AID-ANIE2727>3.0.CO;2-I     Document Type: Article

References (22)

1. I. Fleming, Comprehensive Organic Synthesis Vol. 2 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, pp. 576-594;
2. b) P. Mangeney, Tetrahedron: Asymmetry 1990, 8, 477.
3. M. H. D. Postema, C-glycoside synthesis, CRC, Boca Raton, FL, 1995;
4. b) E. D. Levy, C. Tang. The chemistry of C-glycosides, Pergamon, Oxford, 1995;
5. c) For the synthesis of 2.5-disubstituted tetrahydrofurans, see J. C. Harmange, B. Figadere. Tetrahedron: Asymmetry 1993, 4, 1711-1754.
6. For six-membered-ring oxocarbenium ions, see T. Harada, T. Nakamura, M. Kinugasa, A. Oku, J. Org. Chem. 1999, 64, 7594-7600, and references therein: T. Sammakia, R. S. Smith. J. Am. Chem. Soc. 1992, 114, 10998-10999; S. E. Denmark, N. G. Almstead, J. Am. Chem. Soc. 1991, 113, 8089-8110.
7. For six-membered-ring oxocarbenium ions, see T. Harada, T. Nakamura, M. Kinugasa, A. Oku, J. Org. Chem. 1999, 64, 7594-7600, and references therein: T. Sammakia, R. S. Smith. J. Am. Chem. Soc. 1992, 114, 10998-10999; S. E. Denmark, N. G. Almstead, J. Am. Chem. Soc. 1991, 113, 8089-8110.
8. For six-membered-ring oxocarbenium ions, see T. Harada, T. Nakamura, M. Kinugasa, A. Oku, J. Org. Chem. 1999, 64, 7594-7600, and references therein: T. Sammakia, R. S. Smith. J. Am. Chem. Soc. 1992, 114, 10998-10999; S. E. Denmark, N. G. Almstead, J. Am. Chem. Soc. 1991, 113, 8089-8110.
9. For five-membered-ring oxocarbenium ions, see a) C. H. Larsen, B. H. Ridway, J. T. Shaw, K. A. Woerpel, J. Am. Chem. Soc. 1999, 121, 12208-12209; J. T. Shaw, K. A. Woerpel, Tetrahedron 1999, 55, 8747-8756; b) A. Schmitt, H.-U. Reissig. Synlett 1990, 40-42.
10. For five-membered-ring oxocarbenium ions, see a) C. H. Larsen, B. H. Ridway, J. T. Shaw, K. A. Woerpel, J. Am. Chem. Soc. 1999, 121, 12208-12209; J. T. Shaw, K. A. Woerpel, Tetrahedron 1999, 55, 8747-8756; b) A. Schmitt, H.-U. Reissig. Synlett 1990, 40-42.
11. For five-membered-ring oxocarbenium ions, see a) C. H. Larsen, B. H. Ridway, J. T. Shaw, K. A. Woerpel, J. Am. Chem. Soc. 1999, 121, 12208-12209; J. T. Shaw, K. A. Woerpel, Tetrahedron 1999, 55, 8747-8756; b) A. Schmitt, H.-U. Reissig. Synlett 1990, 40-42.
12. For acyclic acetals, see K. Manju, S. Trehan, Chem. Commun. 1999, 1929-1930.
13. P. Collins, R. Ferrier, Monosacharides: Their chemistry and their roles in Natural Products, Wiley. New York, 1995;
14. b) A. Cavé, D. Cortés, B. Frigadere, R. Hocquemiller, O. Laprévot, A. Laurens, M. Leboeuf, Phytochemical Potential of Tropical Plants; Recent Advances in Phytochemistry. Vol. 27 (Eds.: K. R. Bownum, J. Romeo, H. H. A. Stafford), Plenum, New York, 1993.
15. Many stereocontrolled approaches to these structures have been reported. Among them, nucleophilic substitution at the anomeric center of a furanoid glycal or a furanosyl halide appears to be a general strategy for preparing the corresponding 2-substituted tetrahydrofuran (see ref. [2]).
16. P. Armas, F. García-Tellado, J. J. Marrero-Tellado, J. Robles, Tetrahedron Lett. 1998, 39, 131-134.
17. [4a] or by using the protocal of Suárez et al., which entails the rearrangement of a suitable 2,3-O-isopropylidene-protected luranoside to the required 1.2-protected one.[12]
18. After work-up and chromatography no other diastereomers could be isolated or detected. The configuration assigned to each newly created stereogenic center was continued by nOe spectroscopic analysis.
19. P. Kozikowski, K. L. Sorgi, Tetrahedron Lett. 1983, 24, 1563-1566.
20. P. Armas, C. G. Francisco, E. Suárez, J. Am. Chem. Soc. 1993, 115, 8865-8866.
21. [14] The bicycle does not seem tro play a special role in the stereochemical outcome of these reactions, and the 1,3-syn stereoselectivity observed is in total accordance with the stereoelectronic model proposed by Woerpel et al.[4]
22. V. Jaouen, A. Jégou, L. Lemée, A. Veyrières, Tetrahedron 1999, 55, 9245-9260.