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Volumn 84, Issue 10, 2006, Pages 1208-1217

Mechanism of cyclopropanol to cyclopropanol isomerization mediated by Ti(IV) and a Lewis acid

Author keywords

Cyclopropanol; Kulinkovich hydroxycyclopropanation; Titanium isopropoxide

Indexed keywords

CYCLOPROPANOL; KULINKOVICH HYDROXYCYCLOPROPANATION; LEWIS ACIDS; TITANIUM ISOPROPOXIDE;

EID: 33847635626     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-069     Document Type: Article
Times cited : (7)

References (37)
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    • It has been demonstrated elsewhere (3a, 3d, 4) and observed in our lab that the Kulinkovich hydroxycyclopropanation yields exclusively cyclopropanol isomer 1, bearing phenyl cis to methyl and does not give any of isomer 2, where phenyl is trans to methyl. The origin of this stereochemical preference has been addressed computationally. Y.-D. Wu and Z.-X. Yu. J. Am. Chem. Soc. 123, 5777 2001
    • It has been demonstrated elsewhere (3a, 3d, 4) and observed in our lab that the Kulinkovich hydroxycyclopropanation yields exclusively cyclopropanol isomer 1, bearing phenyl cis to methyl and does not give any of isomer 2, where phenyl is trans to methyl. The origin of this stereochemical preference has been addressed computationally. Y.-D. Wu and Z.-X. Yu. J. Am. Chem. Soc. 123, 5777 (2001).
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    • Transmetallation with inversion of configuration at carbon has been observed, (a) Sn to Pd: J.W. Labadie and J.K. Stille. J. Am. Chem. Soc. 105, 669 (1983);
    • Transmetallation with inversion of configuration at carbon has been observed, (a) Sn to Pd: J.W. Labadie and J.K. Stille. J. Am. Chem. Soc. 105, 669 (1983);
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    • (c) Li to Zn: S. Klein, I. Marek, and J.-F. Normant. J. Org. Chem. 59, 2925 (1994);
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    • Li to Hg: C. Strohmann, B.C. Abele, K. Lehmen, F. Villafañe, L. Sierra, S. Martín-Barrios, and D. Schildbach. J. Organomet. Chem. 661, 149 (2002).
    • (e) Li to Hg: C. Strohmann, B.C. Abele, K. Lehmen, F. Villafañe, L. Sierra, S. Martín-Barrios, and D. Schildbach. J. Organomet. Chem. 661, 149 (2002).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.