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Volumn 50, Issue 26, 2011, Pages 5938-5942

Sequential transformations to access polycyclic chemotypes: Asymmetric crotylation and metal carbenoid reactions

Author keywords

carbenoids; cyclization; diastereoselectivity; diversity oriented synthesis; sequential transformations

Indexed keywords

ASYMMETRIC CROTYLATION; CARBENOID REACTION; CARBENOIDS; CHEMOTYPES; DIASTEREO-SELECTIVITY; DIVERSITY-ORIENTED SYNTHESIS; HECK CYCLIZATION; PENTACYCLES; PHOTOCYCLOADDITION; POLYCYCLES; SEQUENTIAL TRANSFORMATIONS;

EID: 79959200320     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101366     Document Type: Article
Times cited : (30)

References (68)
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    • For select recent examples of sequential transformations, see
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    • For select examples, see
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    • For select reviews and seminal papers on diversity-oriented synthesis, see
    • For select reviews and seminal papers on diversity-oriented synthesis, see
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    • note
    • In a control reaction, a 1:1 mixture of diastereomers of 3c afforded product 4c as a 1:1 mixture of diastereomers.
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    • 79959215055 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for complete mechanistic and conformational analyses and NOE measurements.
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    • note
    • X-ray crystal structure analysis was carried out on DMAP salt derivative 6a and acid derivative 7a and 10a. CCDC 808910 (5a), CCDC 809096 (diastereomer of 5a), CCDC 809097 (diastereomer of 5c), CCDC 809098 (6a), CCDC 809099 (7a), CCDC 809100 (8b), and CCDC 809101 (10a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
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    • note
    • A possible mechanism for the partial racemization is provided in the Supporting Information.
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    • note
    • The relative stereochemistry of compound 11 was tentatively assigned based on analogy to compound 12. All efforts to grow suitable crystals of compound 11 have been unsuccessful thus far.
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    • note
    • 2, MeCN, MeOH, acetone, and THF (tetrahydrofuran), all of which resulted in sluggish reactions or significant decomposition.
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    • note
    • Attempts to prepare enantioenriched 2d were unsuccessful because of racemization of the allylic ether under the crotylation reaction conditions.
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    • A structural-similarity search of the framework 13 at ¥90% threshold showed no hits. Structural similarity is measured using the Tanimoto equation and the PubChem. dictionary-based binary fingerprint (http://pubchem.ncbi.nlm. nih.gov/).
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    • (+)-Nodulisporic Acid F
    • (+)-Nodulisporic Acid F


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.