Chirons in the 1,3-dioxane series: Stereospecific cross-coupling reactions and chirality transfers

Tetrahedron Asymmetry

Volumn 9, Issue 10, 1998, Pages 1657-1660

  Amadji, Morad ^a   Cahard, Dominique ^a   Moriggi, Jean Dominique ^a   Toupet, Loïc ^b   Plaquevent, Jean Christophe ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHIRALITY; CONFORMATIONAL TRANSITION; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032557629     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00171-2     Document Type: Article

References (17)

1. (a) J. Vadecard, J. C. Plaquevent, L. Duhamel and P. Duhamel J. Chem. Soc., Chem. Commun. 1993, 116-117.
2. (b) J. Vadecard, J. C. Plaquevent, L. Duhamel, P. Duhamel and L. Toupet J. Org. Chem. 1994, 59, 2285-2286.
3. (c) For the synthesis of prochiral dibrominated precursors, see M. Amadji, J. Vadecard, U. Schimmel, G. Plé and J. C. Plaquevent J. Chem. Res. (S) 1995, 362-363.
4. M. Amadji, J. Vadecard, J. C. Plaquevent, L. Duhamel and P. Duhamel J. Am. Chem. Soc. 1996, 118, 12483-12484.
5. S. Murahashi, M. Yamamura, K. Yanagisawa, N. Mita and K. Kondo J. Org. Chem. 1979, 44, 2408-2417.
6. Ni, Fe, Co and Ag catalysts have already been employed in cross-coupling reactions involving compounds bearing axial chirality. See for example: (a) H. M. Walborsky and R. B. Banks J. Org. Chem. 1981, 46, 5074-5077;
7. (b) I. Erdelmeier and H. J. Gais J. Am. Chem. Soc. 1989, 111, 1125-1126.
8. In a typical experiment, a 1 N solution of the required arylmagnesium bromide in THF (1.3 mmol, 1.3 mL) was added dropwise under argon and at 0°C to dry zinc bromide (1.5 mmol, 338 mg) in THF (3 mL). The mixture was stirred for 2 h at room temperature whereupon the magnesium bromide precipitated. Then a solution of 2-alkyl or 2-aryl-5-bromomethylene-1,3-dioxane (R)-1 (1 mmol) and tetrakis(triphenylphosphine) palladium (0.05 mmol, 58 mg) in THF (2 mL) was added dropwise. The reaction was stirred at room temperature for 3 h and then was diluted with diethyl ether (20 mL). The organic layer was washed with water and the aqueous layer was extracted twice with diethyl ether. The combined organic layers were washed with saturated sodium chloride then dried over anhydrous magnesium sulfate. The solution was filtered, concentrated and the residue was purified by flash chromatography (petroleum ether:diethyl ether=99:1) to give compounds (R)-2.
9. L. Duhamel and J. C. Plaquevent J. Organomet. Chem. 1993, 448, 1-3.
10. G. Fraenkel, S. Dayagi and S. Kobayashi J. Phys. Chem. 1968, 72, 953-961.
11. (a) M. Tamura and J. K. Kochi J. Am. Chem. Soc. 1971, 93, 1487-1489;
12. (b) S. M. Neumann and J. K. Kochi J. Org. Chem. 1975, 40, 599-606.
13. Organozinc reagents have already exhibited high efficiency in such reactions. For reviews, see: (a) J. Tsuji Palladium Reagents and Catalysts. Innovation in Organic Synthesis; John Wiley & Sons: New York, 1995;
14. (b) E. Erdik Tetrahedron 1992, 44, 9577-9648;
15. (c) P. Knochel and R. D. Singer Chem. Rev. 1993, 93, 2117-2188.
16. The full details of the X-ray crystallographic data have been deposited at the Cambridge Crystallographic Data Centre.
17. In a typical experiment, a solution of the compound (R)-2 (0.25 mmol) in THF (0.5 mL) was added at room temperature to a solution of potassium tert-butoxide (1.5 mmol, 170 mg) and tert-butanol (1.1 mmol, 0.1 mL) in THF (9 mL). The reaction was stirred at room temperature for 12 h and was then neutralized with saturated sodium hydrogencarbonate. The aqueous layer was extracted with diethyl ether and the combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. Purification of the residue by flash chromatography (petroleum ether:diethyl ether=90:10) gave the pure 3 derivative.