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Volumn 55, Issue 47, 2016, Pages 14663-14667

Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch 725674

Author keywords

1,3 diols; diboration; homologation; lithiation; Sch 725674

Indexed keywords

ENANTIOSELECTIVITY;

EID: 84995602233     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201608406     Document Type: Article
Times cited : (53)

References (61)
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    • When using a substrate bearing a carbamate as the leaving group and an OTBS group at the β position, β-elimination competes with 1,2-migration with a ratio of 13; see the Supporting Information for details
    • E. Vedrenne, O. A. Wallner, M. Vitale, F. Schmidt, V. K. Aggarwal, Org. Lett. 2009, 11, 165–168. When using a substrate bearing a carbamate as the leaving group and an OTBS group at the β position, β-elimination competes with 1,2-migration with a ratio of 1:3; see the Supporting Information for details.
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    • C−Si moieties can also be used as masked alcohols for homologation reactions; see
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    • The selective homologation of 1,2-bis(catechol boronic esters) with TMSCHN2has been reported; see: M. Kalendra, R. A. Dueñes, J. P. Morken, Synlett 2005, 1749–1751. However, we have shown that the corresponding 1,2-bis(pinacol boronic esters), which are less electrophilic, do not react with TMSCHN2; see the Supporting Information for details.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.