Catalytic asymmetric reaction with water: Enantioselective synthesis of α-hydroxyesters by a copper-carbenoid O-H insertion reaction

Angewandte Chemie - International Edition

Volumn 47, Issue 5, 2008, Pages 932-934

  Zhu, Shou Fei ^a   Chen, Chao ^b   Cai, Yan ^a   Zhou, Qi Lin ^a  

^a NANKAI UNIVERSITY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Asymmetric catalysis; Carbenoids; Hydroxyesters; Insertion; Water

Indexed keywords

ENANTIOSELECTIVITY; ESTERS; LIGANDS; REACTION KINETICS;

ASYMMETRIC REACTIONS; CARBENOIDS; HYDROXYESTERS;

CATALYST ACTIVITY;

COPPER; ESTER; SPIRO COMPOUND; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COPPER; ESTERS; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM; WATER;

EID: 38549171363     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704651     Document Type: Article

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18. - = tetrakis[3,5-bis(trifluoromethyl)phenyl] borate.
19. Ph-box = 2,2′-bis(4,5-dihydro-4-phenyloxazol-2-yl)propane.
20. iPr-pybox = 2,6-bis(4,5-dihydro-4-isopropyloxazol-2-yl)pyridine.
21. Ph-binabox = 2,2′-bis(4,5-dihydro-4-phenyloxazol-2-yl)-1,1′- binaphthyl.
22. binap = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl.
23. sdp = 7,7′-bis(diphenylphosphino)-1,1′-spirobiindane.
24. phox = 2-(2-diphenylphosphinophenyl)-4,5-dihydro-4-isopropyloxazole.
25. siphox = 7-diphenylphosphino-7′-(4,5-dihydro-4-phenyloxazol-2-yl)- 1,1′-spirobiinane.
26. Because the reaction is biphasic, the amount of water used has a negligible influence on the yield and enantioselectivity.
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