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Volumn , Issue 11, 2008, Pages 1724-1728

Synthesis of enantioenriched N-aryl-2-pyridones with chiral C-N axes by rhodium-catalyzed [2+2+2] cycloaddition of alkynes with isocyanates

(4) Tanaka, Ken a Takahashi, Yoshihiro a Suda, Takeshi a Hirano, Masao a

a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY (Japan)

Author keywords

Alkynes; Cycloaddition; Isocyanates; Pyridones; Rhodium

Indexed keywords

ALKYNE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; PYRIDONE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 48249134040 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078488 Document Type: Article

Times cited : (72)

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- General Procedure for the [2+2+2] Cycloaddition (Tables 2 and 3) Under an Ar atmosphere, a CH2Cl2 solution (0.5 mL) of (R)-BINAP (0.010-0.040 mmol, 5-20 mol, was added to a CH 2Cl2 solution (0.5 mL) of [Rh(cod)2]BF 4 (0.010-0.040 mmol, 5-20 mol, at r.t, and the mixture was stirred for 5 min. The resulting solution was stirred under H2 (1 atm) at r.t. for 1 h, concentrated to dryness, and dissolved in CH2Cl 2 (0.4 mL, To this solution was added a CH2Cl2 solution (0.7 mL) of 2 (0.220 mmol) and then a CH2Cl 2 solution (0.9 mL) of 1 (0.200 mmol) at r.t. After stirring at r.t. for 1-18 h, the resulting solution was concentrated and product 3 was isolated by a silica gel chromatography. Compound, )-3aa: colorless solid; mp 46.3-47.1 °C; [α]D25 +44.7 c 1.46, CHCl
- R = 18.5 min (minor isomer) and 21.2 min (major isomer).

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