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Volumn 29, Issue 9, 2010, Pages 2126-2131

Ruthenium-catalyzed enantioselective [3+3] cycloaddition of propargylic alcohols with 2-naphthols

Author keywords

[No Author keywords available]

Indexed keywords

2-NAPHTHOLS; ALLENYLIDENES; CYCLOADDITION PRODUCTS; ENANTIOSELECTIVE; GOOD YIELD; HIGH ENANTIOSELECTIVITY; INTRAMOLECULAR CYCLIZATIONS; PROPARGYLATION; PROPARGYLIC ALCOHOLS; REACTIVE INTERMEDIATE; STEPWISE REACTION; VINYLIDENE COMPLEXES;

EID: 77951853107     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100097k     Document Type: Article
Times cited : (68)

References (48)
  • 9
    • 33745777313 scopus 로고    scopus 로고
    • For recent reviews of transition metal-allenylidene complexes, see
    • For recent reviews of transition metal-allenylidene complexes, see: Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2006, 45, 2176
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2176
    • Bruneau, C.1    Dixneuf, P.H.2
  • 33
    • 77951769965 scopus 로고    scopus 로고
    • No formation of the cycloaddition product 3a was observed, but instead the corresponding propargylated naphthol was obtained in 39% yield with 51% ee (R). This result indicates that propargylation of 2-naththol proceeded enantioselectively when 1b was used as a catalyst
    • No formation of the cycloaddition product 3a was observed, but instead the corresponding propargylated naphthol was obtained in 39% yield with 51% ee (R). This result indicates that propargylation of 2-naththol proceeded enantioselectively when 1b was used as a catalyst.
  • 40
    • 0000042251 scopus 로고    scopus 로고
    • The first example of an asymmetric reaction via a chiral ruthenium-vinylidene complex was reported by our group; see
    • The first example of an asymmetric reaction via a chiral ruthenium-vinylidene complex was reported by our group; see: Nishibayashi, Y.; Takei, I.; Hidai, M. Organometallics 1997, 16, 3091
    • (1997) Organometallics , vol.16 , pp. 3091
    • Nishibayashi, Y.1    Takei, I.2    Hidai, M.3
  • 42
    • 77951841234 scopus 로고    scopus 로고
    • We previously observed no kinetic resolution in the ruthenium-catalyzed enantioselective propargylation of aromatic compounds. (8a) On the basis of this result, we consider that the chirality at the propargylic position of the propargylic alcohols did not affect the reactivity of propargylic alcohols in this ruthenium-catalyzed enantioselective cycloaddition because the first step of the cycloaddition reaction is the propargylation of aromatic compounds
    • We previously observed no kinetic resolution in the ruthenium-catalyzed enantioselective propargylation of aromatic compounds. (8a) On the basis of this result, we consider that the chirality at the propargylic position of the propargylic alcohols did not affect the reactivity of propargylic alcohols in this ruthenium-catalyzed enantioselective cycloaddition because the first step of the cycloaddition reaction is the propargylation of aromatic compounds.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.