Pd-catalyzed asymmetric sulfinylzincation of 1-alkynoates using 1-alkynyl sulfoxides bearing a chiral auxiliary

Tetrahedron Asymmetry

Volumn 13, Issue 18, 2002, Pages 1961-1964

  Maezaki, Naoyoshi ^a   Yagi, Suguru ^a   Ohsawa, Shizuka ^a   Ohishi, Hirofumi ^b   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; SULFOXIDE; VINYL DERIVATIVE; ZINC;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; DIASTEREOISOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037145005     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00548-7     Document Type: Article

References (12)

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2. Perlmutter P. Baldwin J.E., Magnus P.D., Conjugate Addition Reactions in Organic Synthesis. 9:1992;353-354 Pergamon Press, Oxford. and references cited therein.
3. Aversa M.C., Barattucci A., Bonaccorsi P., Giannetto P., Policicchio M. J. Org. Chem. 66:2001;4845-4851.
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5. Aversa M.C., Barattucci A., Bonaccorsi P., Giannetto P., Jones D.N. J. Org. Chem. 62:1997;4376-4384.
6. Reports regarding sulfenyl anion, see: Furukawa, N.; Konno, Y.; Tsuruoka, M.; Fujihara, H.; Ogawa, S. Chem. Lett. 1989, 1501-1504; Hogg, D. R.; Stewart, J. J. Chem. Soc., Perkin Trans. 2 1974, 43-47.
7. Reports regarding sulfenyl anion, see: Furukawa, N.; Konno, Y.; Tsuruoka, M.; Fujihara, H.; Ogawa, S. Chem. Lett. 1989, 1501-1504; Hogg, D. R.; Stewart, J. J. Chem. Soc., Perkin Trans. 2 1974, 43-47.
8. Goodridge R.J., Hambley T.W., Haynes R.K., Ridley D.D. J. Org. Chem. 53:1988;2881-2889.
9. Hirano M., Yakabe S., Ando K., Morimoto T. J. Chem. Res. (S). 1998;816-817.
10. Youn J.-H., Herrmann R. Tetrahedron Lett. 27:1986;1493-1494.
11. s)-configuration, since the nucleophilic reaction to sulfenates is known to proceed with inversion at the stereogenic center, see: Walker A.J. Tetrahedron: Asymmetry. 3:1992;961-998. and references cited therein.
12. . Similar diastereoselectivity was observed in the oxidation of 3-exo-(alkenylthio)isoborneols, and explained by hydrogen bonding of the 2-OH group with m-CPBA, see: Yang T.-K., Chu H.-Y., Lee D.-S., Jiang Y.Z., Chou T.-S. Tetrahedron Lett. 37:1996;4537-4540.