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Volumn 70, Issue 1, 1997, Pages 207-217

N,N,N′,N′-Tetraalkyl-2,2′-dihydroxy-1,1′- binaphthyl-3,3′-dicarboxamides: Novel Chiral Auxiliaries for Asymmetric Simons-Smith Cyclopropanation of Allylic Alcohols and for Asymmetric Diethylzinc Addition to Aldehydes

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EID: 0000872931     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.207     Document Type: Article
Times cited : (125)

References (60)
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    • For other diastereoselective cyclopropanations, see: a) T. Imai, H. Mineta, and S. Nishida, J. Org. Chem., 55, 4986 (1990); b) A. Sele, B. Baehler, and J. M. J. Tronchet, Helv. Chim. Acta, 62, 866 (1979); c) T. Morikawa, H. Sasaki, K. Mori, M. Shiro, and T. Taguchi, Chem. Pharm. Bull., 40, 3189 (1992); d) T. Morikawa, H. Sasaki, R. Hanai, A. Shibuya, and T. Taguchi, J. Org. Chem., 59, 97 (1994); e) R. Murali, C. V. Ramana, and M. Nagarajan, J. Chem. Soc., Chem. Commun., 1995, 217, and references cited therein.
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    • For other diastereoselective cyclopropanations, see: a) T. Imai, H. Mineta, and S. Nishida, J. Org. Chem., 55, 4986 (1990); b) A. Sele, B. Baehler, and J. M. J. Tronchet, Helv. Chim. Acta, 62, 866 (1979); c) T. Morikawa, H. Sasaki, K. Mori, M. Shiro, and T. Taguchi, Chem. Pharm. Bull., 40, 3189 (1992); d) T. Morikawa, H. Sasaki, R. Hanai, A. Shibuya, and T. Taguchi, J. Org. Chem., 59, 97 (1994); e) R. Murali, C. V. Ramana, and M. Nagarajan, J. Chem. Soc., Chem. Commun., 1995, 217, and references cited therein.
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    • and references cited therein
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    • note
    • When compound 1a (0.5 mmol) was treated with diethylzinc (0.5 mmol) in dichloromethane, evolution of ethane (17 ml, 0.76 mmol) was detected and NMR analysis of the reaction mixture indicated that about 0.22 mmol of ethane dissolved in dichloromethane. Thus, all the amount of evolved ethane was estimated to be about twice molar amount (0.98 mmol).
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    • note
    • Lewis acidic zinc cation should be solvated in the solution.
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    • note
    • Denmark et al. have found linear relationship between the %ee of the chiral auxiliary and the %ee of the product in asymmetric Simmons-Smith reaction using (1R, 2R)-1,2-bis(toluenesulfonyl-amino)cyclohexane as a chiral auxiliary (Ref. 8f).
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    • note
    • 2 to give iodomethylzine allyloxide has been reported to be slow (Ref. 11).
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    • Chiral titanium catalysts show high enantioselectivity in the reaction of alkynyl aldehydes: a) D. Seehach, A. K. Beck, B. Schmidt, and Y. M. Wang, Tetrahedron, 50, 4363 (1994); b) H. Lütlens, S. Nowotny, and P. Knochel, Tetrahedron Asymmetry, 6, 2675 (1995); c) N. Oguni, N. Satoh, and H. Fujii, Synlett, 1995, 1043.
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    • For the review of asymmetric reactions using 3,3′-substituted binaphthol as a chiral auxirialy, see: K. Ishihara and H. Yamamoto, "In Advances in Catalytic Processes," ed by P. M. Doyle, JAI Press. London (1995), Vol. 1, p.29.
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    • During the preparation of this manuscript, synthesis of (S)-2, 2′-bis(methoxymethoxy)-1,1′-binaphthyl was reported: H. T. Stock and R. M. Kellogg, J. Org. Chem., 61, 3093 (1996).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.