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Volumn 14, Issue 12, 2009, Pages 5216-5222

A striking exception to the chelate model for acyclic diastereocontrol: Efficient access to a versatile propargyl alcohol for chemical synthesis

Author keywords

Acyclic diastereocontrol; Chiral building block; Felkin Anh; Pantolactone; Synthesis

Indexed keywords

ALKYNE; CHELATING AGENT; PROPANOL; PROPARGYL ALCOHOL;

EID: 73849096534     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14125216     Document Type: Article
Times cited : (5)

References (14)
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    • Paraphrase of the Chinese philosopher, Lao Tzu, The journey of a thousand miles begins beneath one's feet. The more common translation of the proverb is, The journey of a thousand miles begins with a single step.
    • Paraphrase of the Chinese philosopher, Lao Tzu, "The journey of a thousand miles begins beneath one's feet." The more common translation of the proverb is, "The journey of a thousand miles begins with a single step."
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    • Evans, D.A.1    Welch, D.S.2    Speed, A.W.H.3    Moniz, G.A.4    Reichelt, A.5    Ho, S.6
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    • Electronegative atoms (e.g., oxygen) are often good Lewis bases, so manipulation of the system in either direction (-OR as large or medium group) is frequently possible by promoting or disrupting chelation of metal salts; see reference [4] for discussion.
    • Electronegative atoms (e.g., oxygen) are often good Lewis bases, so manipulation of the system in either direction (-OR as "large" or "medium" group) is frequently possible by promoting or disrupting chelation of metal salts; see reference [4] for discussion.
  • 6
    • 73849105131 scopus 로고    scopus 로고
    • The products arising from the alternative conformations are sometimes referred to as Felkin and anti-Felkin products, although the Felkin-Anh model accounts for either possibility. In this paper we use the term chelation control to indicate products arising from the electron-rich Lewis basic substituent occupying the medium position in the Felkin-Anh model
    • The products arising from the alternative conformations are sometimes referred to as "Felkin" and "anti-Felkin" products, although the Felkin-Anh model accounts for either possibility. In this paper we use the term "chelation control" to indicate products arising from the electron-rich Lewis basic substituent occupying the "medium" position in the Felkin-Anh model.
  • 7
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    • CCDC 748703 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html/ or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223 336033; E-Mail: deposit@ccdc.cam.ac.uk.
    • CCDC 748703 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html/ or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223 336033; E-Mail: deposit@ccdc.cam.ac.uk.
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    • Additional amounts of 1 can be extracted from the mother liquor, as desired.
    • Additional amounts of 1 can be extracted from the mother liquor, as desired.
  • 9
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    • Akhoon, K.D.1    Myles, D.C.2
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    • Convergent Total Synthesis of (+)-Mycalamide A
    • and references cited therein. On the other hand, poor selectivity in such systems has also been reported; for example and discussion see
    • On the other hand, poor selectivity in such systems has also been reported; for example and discussion see: Kagawa, N.; Ihara, M.; Toyota, M. Convergent Total Synthesis of (+)-Mycalamide A. J. Org. Chem. 2006, 71, 6796-6805, and references cited therein.
    • (2006) J. Org. Chem , vol.71 , pp. 6796-6805
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    • Addition of a vinyl Grignard nucleophile to aldehyde 7 produced a complex mixture of products for which purification was not attempted.
    • Addition of a vinyl Grignard nucleophile to aldehyde 7 produced a complex mixture of products for which purification was not attempted.
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    • Our lab has documented and exploited the minimal steric profile of acetylide nucleophiles in the olefination of hindered aldehydes and ketones; see: Engel, D.A, Dudley, G.B. Olefination of ketones using a gold(III)-catalyzed meyer-schuster rearrangement. Org. Lett. 2006, 8, 4027-4029
    • Our lab has documented and exploited the minimal steric profile of acetylide nucleophiles in the olefination of hindered aldehydes and ketones; see: Engel, D.A.; Dudley, G.B. Olefination of ketones using a gold(III)-catalyzed meyer-schuster rearrangement. Org. Lett. 2006, 8, 4027-4029.
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    • Lewis acid-catalyzed Meyer-Schuster reactions: Methodology for the olefination of aldehydes and ketones
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    • Engel, D.A.1    Lopez, S.S.2    Dudley, G.B.3
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    • The Meyer-Schuster rearrangement for the synthesis of α,β-unsaturated carbonyl compounds
    • Engel, D.A.; Dudley, G.B. The Meyer-Schuster rearrangement for the synthesis of α,β-unsaturated carbonyl compounds. Org. Biomol. Chem. 2009, 7, 4149-4158
    • (2009) Org. Biomol. Chem , vol.7 , pp. 4149-4158
    • Engel, D.A.1    Dudley, G.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.