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Volumn 72, Issue 12, 2007, Pages 4378-4389

A highly regio- and stereoselective formation of bicyclo[4.2.0]oct-5-ene derivatives through thermal intramolecular [2 + 2] cycloaddition of allenes

Author keywords

[No Author keywords available]

Indexed keywords

COPLANAR ALLYL RADICALS; CYCLOADDUCTS; DIOXANES; DOUBLE BONDS;

EID: 34250158080     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0700528     Document Type: Article
Times cited : (75)

References (91)
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    • The compounds having the bicyclo[4.2.0]octane skeleton constitute an important class of molecules in synthetic and natural product chemistry. For example, see: (a) Piers, E.; Lu, Y.-F. J. Org. Chem. 1989, 54, 2267-2268.
    • The compounds having the bicyclo[4.2.0]octane skeleton constitute an important class of molecules in synthetic and natural product chemistry. For example, see: (a) Piers, E.; Lu, Y.-F. J. Org. Chem. 1989, 54, 2267-2268.
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    • For a reason that is unclear, preparation of 23-derived aldehyde having an NH group by oxidation of the corresponding alcohol was not reproductive.
    • For a reason that is unclear, preparation of 23-derived aldehyde having an NH group by oxidation of the corresponding alcohol was not reproductive.
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    • Mitsunobu condensation with the corresponding alcohols required higher reaction temperature, which makes control of the selective alkylation (without causing [2, 2] cycloaddition) difficult
    • Mitsunobu condensation with the corresponding alcohols required higher reaction temperature, which makes control of the selective alkylation (without causing [2 + 2] cycloaddition) difficult.
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    • However, these result does not conflict with the biradical mechanism depicted in Schemes 14 and 15, because intramolecular coupling or biradicals such as 94 and 101 to the corresponding cyclobutanes would be extremely fast.
    • However, these result does not conflict with the biradical mechanism depicted in Schemes 14 and 15, because intramolecular coupling or biradicals such as 94 and 101 to the corresponding cyclobutanes would be extremely fast.
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    • Formation of the same framework (3-azabicyclo[4.2.0]oct-5-ene) via intermolecular [2 + 2] cycloaddition of in situ-generated cyclic amino allenes with styrene was reported: Christl, M.; Braun, M.; Wolz, E.; Wagner, W. Chem. Ber. 1994, 127, 1137-1142.
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    • In order to determine the relative configuration between C-4 and C-1 (or C-4 and C-8), transformation of 11a and 67 to the corresponding saturated analogues 68 and 69 was desirable. We could unambiguously confirm the relative configuration of 68 and 69 by NOEs including that of the introduced hydrogens at C-5 and C-6. For more details, see the Supporting Information
    • In order to determine the relative configuration between C-4 and C-1 (or C-4 and C-8), transformation of 11a and 67 to the corresponding saturated analogues 68 and 69 was desirable. We could unambiguously confirm the relative configuration of 68 and 69 by NOEs including that of the introduced hydrogens at C-5 and C-6. For more details, see the Supporting Information
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.