SCOPUS 정보 검색 플랫폼

Volumn , Issue 1, 2007, Pages 63-66

A gold(III)-catalyzed double Wacker-type reaction of 1,1-diethynyl acetate

(7) Kato, Keisuke a Teraguchi, Ryuhei a Kusakabe, Taichi a Motodate, Satoshi a Yamamura, Shigeo a Mochida, Tomoyuki a Akita, Hiroyuki a

a TOHO UNIVERSITY (Japan)

Author keywords

1,1 diethynyl acetates; Catalyst; Double Wacker type reaction; Gold; Platinum

Indexed keywords

1,1 DIETHYNYL ACETATE; ACETIC ACID DERIVATIVE; ACETYLENE DERIVATIVE; GOLD; OXYGEN; PLATINUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 33846560312 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2006-956497 Document Type: Article

Times cited : (15)

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39
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- Preparation of Substrates 2; General Procedure: To a solution of trimethylsilyl acetylene (3.32 g, 33.8 mmol) in THF (30 mL) under Ar was added n-BuLi (13.0 mL of 2.6 M in hexane, 33.8 mmol) at -78 °C and the mixture was stirred for 0.5 h at 0 ° C. After the solution was cooled to -78 °C, the corresponding ester 1 (11.3 mmol) in THF (3 × 8 mL) was slowly added dropwise. The mixture was stirred at -10 °C for 12 h and quenched with H2O (80 mL) and EtOAc (80 mL, The organic layers were separated, the aqueous layer was extracted with EtOAc (50 mL, and combined organic layers were dried with MgSO4 and concentrated in vacuo. To a solution of the crude product in THF (30 mL) was added TBAF (22.4 mL of 1 M in THF, 22.4 mmol) and the mixture was stirred for 0.5 h at r.t. The mixture was diluted with H2O (80 mL) and EtOAc (80 mL, The organic layers were separated, the aqueous layer was extracted with EtOAc 2 × 50 mL
- 2: C, 79.62; H, 6.24

40
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- Reaction of 2; General Procedure: A 20-mL round-bottomed flask, containing a magnetic stirring bar, catalyst (0.015 mmol, 2 (0.3 mmol) and MeOH (5 mL) was fitted with a Dimroth condenser capped with a rubber septum. After being stirred for a certain period at 60 °C, the mixture was diluted with EtOAc (20 mL) and washed with aq 3% NaHCO3 (20 mL, The organic layers were separated, the aqueous layer was extracted with EtOAc (30 mL, and combined organic layers were dried with MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography on silica gel. The fraction eluted with hexane-EtOAc(100:1-50:1 and 10:1) afforded 3 and 4, respectively. 3a: colorless oil. 1H NMR (CDCl 3, δ, 1.69-1.78 (m, 1 H, 1.91-2.00 (m, 1 H, 2.22 (s, 3 H, 2.43 (dd, J, 4.4, 16.8 Hz, 1 H, 2.58-2.62 (m, 2 H, 2.80 (dd, J, 9.6, 16.8 Hz, 1 H, 2.99-3.07 (m, 1 H, 3.66 s, 3 H, 7.15
- -1.

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