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Volumn 348, Issue 10-11, 2006, Pages 1171-1182

Preparation of a privileged silicon-stereogenic silane: Classical versus kinetic resolution

Author keywords

Alcohols; Asymmetric catalysis; Copper; Kinetic resolution; Silicon

Indexed keywords


EID: 33746752175     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606071     Document Type: Article
Times cited : (81)

References (50)
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    • To the best of our knowledge, a single kinetic resolution process of racemic silyl ethers based on the reductive cleavage of the silicon-oxygen bond by chiral hydride reagents has been reported so far. However, enantiomeric excesses were determined from the optical rotatory power, which emerges as being sensitive towards impurities of the chiral ligand. In our hands, application of this method to a derivative of rac-5 provided only marginal optical enrichment (< 1% ee): a) A. Holt, A. W. P. Jarvis, G. J. Jarvis, Tetrahedron Lett. 1968, 4087-4088;
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    • note
    • A catalytic asymmetric access as depicted in Scheme 2 was not considered since the synthesis of the requisite precursor, 1,2,3,4-tetrahydro-1- silanaphthalene, has not been accomplished yet.
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    • Diploma Thesis, Albert-Ludwigs-Universität, Freiburg
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    • [29b] has been previously used: a) C. Lorenz, U. Schubert, Chem. Ber. 1995, 128, 1267-1269;
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    • note
    • [27]
  • 50
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    • note
    • [7] is reproduced incorrectly.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.