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Volumn 16, Issue 32, 2010, Pages 9864-9873

Pyrrole and oligopyrrole synthesis by 1,3-dipolar cycloaddition of azomethine ylides with sulfonyl dipolarophiles

Author keywords

Cycloaddition; Oligomerization; Pyrroles; Sulfones; Ylides

Indexed keywords

AZOMETHINE YLIDES; DIPOLAR CYCLOADDITIONS; DIPOLAROPHILES; FUNCTIONALIZED; OLIGOPYRROLES; PYRROLES; SULFONES; SULFONYL GROUPS; YLIDES;

EID: 77955863073     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000742     Document Type: Article
Times cited : (42)

References (162)
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    • For a review on intramolecular dipolar cycloaddition of azomethine ylides describing many examples of pyrrole synthesis with alkynyl. dipolarophiles, see: a) I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765;
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    • For the application of dipolarophiles 4 and 3 in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloadditions with azomethine ylides, see: a) A. López-Pérez, J. Adrio, J.C. Carretero, Angew. Chem. 2009, 121, 346;
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    • The opposite regiochemical outcome in the Ag-catalyzed (controlled by the sulfonyl group) and Cu-catalyzed cycloaddition (controlled by the acetyl group) could be due, at least in part, to the highly oxophilic nature of the copper Lewis acids, which would tend to reinforce the carbonyl regiochemical control
    • The opposite regiochemical outcome in the Ag-catalyzed (controlled by the sulfonyl group) and Cu-catalyzed cycloaddition (controlled by the acetyl group) could be due, at least in part, to the highly oxophilic nature of the copper Lewis acids, which would tend to reinforce the carbonyl regiochemical control.
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    • Regioisomer 10 a can be separated by standard silica gel chromatography, isolated as a single diastereoisomer. For the regiochemical and stereochemical assignment of isomers 8 a and 10 a, see the Supporting Information
    • Regioisomer 10 a can be separated by standard silica gel chromatography, isolated as a single diastereoisomer. For the regiochemical and stereochemical assignment of isomers 8 a and 10 a, see the Supporting Information.
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    • Some interesting types of pyrrole-based natural products, such as prodigiosins and marineosins, present an electronically rich substitution at C-3 in the pyrrole unit
    • Some interesting types of pyrrole-based natural products, such as prodigiosins and marineosins, present an electronically rich substitution at C-3 in the pyrrole unit.
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    • note
    • A minor amount of the exo regioisomer adduct (13%) was detected in the crude reaction mixture. In the case of the preparation of pyrroles 14, a higher overall yield was obtained by previous separation of the pyrrolidine adducts 13, unlike the synthesis of the pyrrole series 9 and 11, in which the crude pyrrolidine intermediates were not purified by silica gel chromatography.
  • 160
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    • note
    • 2, 4 Å molecular sieves, RT, 5 h; then DBU, RT, 30 min. (Figure Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.