Organocatalytic synthesis of terminal propargylamine derivatives by tandem amination-alkynylation

Synlett

Volumn , Issue 20, 2009, Pages 3287-3290

  Wang, Yu ^a   Peng, Fangzhi ^a   Zhang, Hongbin ^a   Shao, Zhihui ^a  

^a YUNNAN UNIVERSITY   (China)

Author keywords

Amination; Organocatalysis; Seyferth Gilbert alkynylation; Tandem reactions; Terminal propargylamines

Indexed keywords

ACETYLENE; ALDEHYDE; AMINE; IMINE; NITROGEN; ORGANIC MATTER; PROPARGYLAMINE; UNCLASSIFIED DRUG;

ALKYNYLATION; AMINATION; ARTICLE; CATALYSIS; DECOMPOSITION; ENANTIOSELECTIVITY; RACEMIZATION; SYNTHESIS;

EID: 72249091062     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218354     Document Type: Article

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52. Typical procedure for one-pot, tandem a-aminationalkynylation of aldehydes: Proline (0.1 mmol, 10 mol%) was added to a stirring solution of aldehyde 1a (1 mmol) and DIAD (1 mmol) in CH2Cl2 (3 mL). After 2 h of vigorous stirring at r.t., MeOH (15 mL), Ohira-Bestmann reagent (1.2 mmol, 1.2 equiv) and K2CO3 (2 mmol, 2 equiv) were added. After stirring for 12 h at r.t., the reaction mixture was diluted with Et2O. The excess solvents were removed under reduced pressure and the residue was purified by flash silica gel chromatography to give the desired product 2a. IR (film): 3254, 2985, 1743, 1678, 1529, 1417, 1233, 1109 cm-1; 1H NMR (300 MHz, CDCl3): d = 6.39 (br s, 1 H), 5.06 (br s, 1 H), 4.89 (sept, J = 6.2 Hz, 2 H), 2.23 (s, 1 H), 1.36 (d, J = 6.9 Hz, 3 H), 1.18 (d, J = 6.1 Hz, 12 H); 13C NMR (75 MHz, CDCl3): d = 156.1, 154.7, 82.1, 71.5, 70.6, 69.8, 45.8, 22.0, 21.9, 19.2; HRMS (ESI): m/z [M + H]+ calcd for C12H20N2O4: 257.1496; found: 257.1490.