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Volumn 45, Issue 21, 2006, Pages 3492-3494

Catalytic enantioselective crossed aldehyde-ketone benzoin cyclization

Author keywords

Asymmetric synthesis; C C coupling; Cyclization; N heterocyclic carbenes; Tertiary alcohols

Indexed keywords

ALCOHOLS; CATALYSIS; KETONES; SALTS; SYNTHESIS (CHEMICAL);

EID: 33745722719     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600268     Document Type: Article
Times cited : (220)

References (46)
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    • note
    • Although the resulting products are more appropriately labeled acyloins rather than benzoins, we have adopted the term benzoin reaction as a general rubric for the nucleophilic addition of aldehydes to carbonyl compounds by the transient intermediacy of an acyl anion equivalent. Although imperfect, this nomenclature avoids confusion with the acyloin reaction, a fundamentally different process that affords otherwise identical products.
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    • note
    • This work was presented in full at the Pacifichem Conference 2005 in Honolulu, Hawaii, USA, December 20, 2005 and the 85th CSJ Spring Meeting in Kanagawa University, Japan, March 26, 2005.
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    • note
    • The absolute configurations of the tertiary alcohols were confirmed by X-ray analysis of the derived (S)-camphanyl esters following studies to confirm the chiral integrity of benzoin products under the esterification conditions (see the Supporting Information for details).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.