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Synlett

Volumn , Issue 2, 2007, Pages 298-302

Enantioselective diels-alder reactions: Effect of the achiral template on reactivity and selectivity

(3) Sibi, Mukund P a Chen, Jianxie a Stanley, Levi a

a NORTH DAKOTA STATE UNIVERSITY (United States)

Author keywords

Achiral template; Chelation; Chiral lewis acid; Diels Alder

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ACRYLIC ACID DERIVATIVE; COPPER; LEWIS ACID; PHENYLBUTAZONE; PYRAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIELS ALDER REACTION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 33847044805 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968014 Document Type: Article

Times cited : (11)

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- General Procedure for the Enantioselective Diels-Alder Reactions. A mixture of 1 (20 mg, 0.055 mmol) and Cu(OTf)2 (18 mg, 0.05 mmol) in CH2Cl2 (2 mL) was stirred at r.t. for 1 h to give a clear green solution. A solution of dienophile (0.5 mmol) in CH 2Cl2 (2 mL) was added at the temperature given in the tables, followed by freshly distilled cyclopentadiene (165 mg, 2.5 mmol, The reaction was monitored by TLC. After completion of the reaction, H2O (2 mL) was added and the mixture was extracted with CH2Cl 2, washed with brine and dried. The solvent was evaporated and the residue was purified by chromatography to give pure product. The endo/exo ratio was evaluated on the basis of 1H NMR spectrum and the enantiomeric purity was determined by HPLC. DA Adduct from Compound 4, α]D25 -176.3 c 2.2, CHCl3, 97% ee estimated on t
- 3): δ = 20.7, 26.4, 26.6, 36.5, 44.3, 47.2, 47.3, 49.7, 52.8, 57.1, 60.8, 127.6, 128.6, 129.1, 131.1, 138.4, 140.0, 171.6, 174.6.

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