Organocatalytic and enantioselective synthesis of β-(hydroxyalkyl)- γ-butyrolactones

Journal of Organic Chemistry

Volumn 73, Issue 10, 2008, Pages 3935-3937

  Hajra, Saumen ^a   Giri, Aswini Kumar ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYST ACTIVITY; ENANTIOSELECTIVITY; GAMMA RAYS; REDUCTION; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVE SYNTHESIS; ORGANOCATALYTIC;

KETONES;

ALDEHYDE; GAMMA BUTYROLACTONE DERIVATIVE; PROLINE;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

4-BUTYROLACTONE; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 43449097862     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8005733     Document Type: Article

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60. In addition to the general procedure, the reaction was carried out under different conditions, e.g., (a) to a suspension of L-proline in dry DMF at 4°C, a solution of aldehydes 2 (1.0 equiv) and n-hexanal 3k (1.0 equiv) was added over 22 h, (b) by changing the mole proportions such as using 2 (2.0 equiv) and 3k (1.0 equiv), and (c) a solution of 2 (2.0 equiv), 3k (1.0 equiv), and proline (0.2 equiv) in dry DMF was stirred at 4°C for overnight. All of the attempts led to an inseparable mixture of products.
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65. int = 0.0264, R1 = 0.0444, wR2 = 0.1020 for 2150 reflections [I > 2σ (I)], Flack(x) parameter = 0.0(10).