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Volumn 22, Issue 26, 2016, Pages 8786-8790

Diastereoselective Coupling of Chiral Acetonide Trisubstituted Radicals with Alkenes

Author keywords

ab initio calculations; alkenes; radical reactions; stereoselectivity

Indexed keywords

CALCULATIONS; HYDROGEN BONDS; REACTION KINETICS; STEREOSELECTIVITY;

EID: 84971673540     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201601957     Document Type: Article
Times cited : (12)

References (34)
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    • the (, R,)-methoxy butenolide, 4, and the chiral radical, as the coupling of the, S, enantiomer of, 4, with the radical generated from, 5 a, gave a 4.01 ratio of the products of, anti, and, syn, addition. The nature of the butenolide radical acceptor and the 40 °C difference in reaction temperature must be responsible for the lower stereoselectivity that we observe compared to that reported by Barton. Our experiments were conducted with the (, R,)-butenolide, 4, because this enantiomer was required for the synthesis of (−)-chromodorolide B.
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    • This lower stereoselectivity observed in the reaction of entry 1 is not a reflection of a chirality mismatch between
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    • A rationale related to the one we advance here was suggested by Gerster and Renauld.
    • [7a].
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    • ; and references [2d], [4], [5] and [9] therein.
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  • 34
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    • The Boltzmann distribution is exponentialsmall energetic errors accumulate 1 kcal mol, error changes the selectivity from 2.31 to 12.3 (±0.5 kcal mol
    • −1).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.