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Volumn 50, Issue 29, 2009, Pages 4212-4216

A new synthesis, including asymmetric synthesis, of alkylidenecyclopropanes by 1,2-CC insertion of cyclobutylmagnesium carbenoides as the key reaction

Author keywords

1,2 CC insertion; Alkylidenecyclopropane; Cyclobutylmagnesium carbenoid; Magnesium carbenoid; Sulfoxide magnesium exchange

Indexed keywords

1 CHLOROCYCLOBUTYL PARA TOLYL SULFOXIDE; 1 CHLOROVINYL PARA TOLYL SULFOXIDE DERIVATIVE; ALKYLIDENECYCLOPROPANE DERIVATIVE; CARBENOID; CARBON; CARBOXYLIC ACID DERIVATIVE; CARBOXYLIC ACID TERTBUTYL ESTER; CHLOROMETHYL PARA TOLYL SULFOXIDE; CYCLOBUTYLMAGNESIUM CARBENOID DERIVATIVE; CYCLOPENTYLMAGNESIUM CHLORIDE; CYCLOPROPANE DERIVATIVE; KETONE; LITHIUM ENOLATE; MAGNESIUM; REAGENT; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

EID: 66149172041     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.038     Document Type: Article
Times cited : (13)

References (47)
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    • Cyclopropanation of chiral-allenic alcohols:
    • Cyclopropanation of chiral-allenic alcohols:. Lautens M., and Delanghe P.H.M. J. Org. Chem. 58 (1993) 5037
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    • Synthesis from enantiomerically pure cyclopropenylcarbinols:
    • Synthesis from enantiomerically pure cyclopropenylcarbinols:. Simaan S., Masarwa A., Bertus P., and Marek I. Angew. Chem., Int. Ed. 45 (2006) 3963
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3963
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    • note
    • Adduct 8 was obtained as a mixture of two diastereomers (the ratio 93:7) with respect to the stereogenic carbon bearing the chlorine atom.
  • 37
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    • note
    • 27ClOS: M, 386.1471. Found; m/z 386.1478.
  • 38
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    • The sulfoxide-magnesium exchange reaction is known to take place with retention of configuration of the carbon bearing a sulfinyl group
    • The sulfoxide-magnesium exchange reaction is known to take place with retention of configuration of the carbon bearing a sulfinyl group. Satoh T., Kobayashi S., Nakanishi S., Horiguchi K., and Irisa S. Tetrahedron 55 (1999) 2515
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    • note
    • 28 +50.5 (c 0.9, EtOH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.