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Synlett

Volumn , Issue 11, 2007, Pages 1656-1662

A two-carbon homologation of aldehydes and ketones using ynamides

(7) You, Lingfeng a Al Rashid, Ziyad F a Figueroa, Ruth a Ghosh, Sunil K a Li, Gang a Lu, Ting a Hsung, Richard P a

a UNIVERSITY OF WISCONSIN MADISON (United States)

Author keywords

E acrylic amides; Oxetene; Torquoselective ring opening; Two carbon homologation; Ynamide

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; AMIDE; KETONE DERIVATIVE; LEWIS ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FEASIBILITY STUDY; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; ROTATION; STEREOCHEMISTRY;

EID: 34447565958 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984513 Document Type: Article

Times cited : (54)

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34
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- General Experimental Procedure: To a solution of ynamide 5 (56.0 mg, 0.30 mmol) in CH2Cl2 (30 mL) was added hexanal (0.055 mL, 0.45 mmol, 1.5 equiv, The solution was then cooled to -78°C and a solution of BF3·OEt2 (0.20 M in CH 2Cl2, 0.75 mL, 0.15 mmol) was added carefully dropwise and the reaction was stirred for 10 min at -78°C. When the TLC analysis showed that the starting ynamide 5 was completely consumed, the reaction mixture was poured into sat aq NaHCO3 (20 mL, The two phases were separated and the aqueous layer was extracted with CH2Cl2 (3 x 20 mL, The organic layers were combined, dried over Na2SO4, and concentrated in vacuo. The resulting crude yellow oil was purified using silica gel flash column chromatography (gradient eluent: 10-20% EtOAc in hexanes) to afford the pure acrylic amide 6 56.0 mg, 65, exclusi
- +.

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44
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- We did not rigorously assign the E and Z stereochemistries for the trisubstituted acrylic amides 23, 24 and 25 because of the low ratio and/or yield
- We did not rigorously assign the E and Z stereochemistries for the trisubstituted acrylic amides 23, 24 and 25 because of the low ratio and/or yield.

45
- 34447508528
- Authors appreciate the suggestion made by one of the referees to attempt homologations with these unsymmetrical ketones
- Authors appreciate the suggestion made by one of the referees to attempt homologations with these unsymmetrical ketones.

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