Chiral terpene auxiliaries II. Spiroborate esters derived from α-pinene - New catalysts for asymmetric borane reduction of prochiral ketones

Tetrahedron Letters

Volumn 52, Issue 30, 2011, Pages 3919-3921

  Krzemiński, Marek P ^a   Ćwiklińska, Marta ^a  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

Pinene; Aminoalcohols; Asymmetric reduction; Borane; Spiroborate esters

Indexed keywords

ACETOPHENONE; BORANE DERIVATIVE; CATECHOL; ESTER DERIVATIVE; ETHYLENE GLYCOL; KETONE DERIVATIVE; PINENE; PROPANE; TERPENE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY;

EID: 79959497033     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.095     Document Type: Article

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25. 3: C, 69.17; H, 9.87; N, 4.03. Found: C, 69.43; H, 9.92; N, 4.21.
26. 2 (10 M, 100 μL, 1 mmol) was added at room temperature with stirring. Next, a solution of ketone (1 mmol) in THF (2 mL) was added at a rate of 3 mL per hour using a syringe pump. The solution was stirred for 20 min and quenched by the addition of MeOH (1 mL) at room temperature. After stirring for 30 min at rt, the solvents were evaporated under vacuum and the product was isolated by column chromatography using hexane/EtOAc (4:1) as eluent.