Lipase/palladium-catalyzed asymmetric transformations of ketoximes to optically active amines

Organic Letters

Volumn 3, Issue 25, 2001, Pages 4099-4101

  Choi, Yoon Kyung ^a   Kim, Mi Jung ^a   Ahn, Yangsoo ^a   Kim, Mahn Joo ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; KETONE; LIPASE B, CANDIDA ANTARCTICA; NOVOZYME 435; OXIME; PALLADIUM; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; OPTICAL ROTATION;

AMINES; KETONES; LIPASE; MOLECULAR STRUCTURE; OPTICAL ROTATION; OXIMES; PALLADIUM; SUPPORT, NON-U.S. GOV'T;

EID: 0035856968     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0168622     Document Type: Article

References (32)

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23. In the racemization, the use of DBN (1,5-diazabicyclo[4.3.0]non-5-ene) or DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as the base gave the better results. However, the enzymatic acylation reaction did not proceed smoothly in the presence of the strong organic bases.
24. Ketoximes were prepared according to the general methods. See: (a) Lachman, A. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, p 70.
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26. 6a mp 98-100°C).
27. 3): 3f, +72.4°; 3g, +83.6°; 3h, +79.2°. It is noted that our optical rotation of 3c has an opposite sign from that of the literature value, indicating that the latter was reported incorrectly.
28. In this case, the steric crowdness in the cyclohexane ring increases going from oxime to amine, and thus the reductive deamination is slightly more favored.
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31. The reductive elimination of amino group is particularly significant when the concentration of amine is high. That is why amines are not good substrates for lipase/ruthenium-catalzyed DKR. The side reaction can be reduced by increasing the amount of enzymes at the cost of ee.
32. Simple imines are expected to be asymmetrically transformed to optically amines by the lipase/ruthenium bi-catalysis. However, simple imines have some disadvantages over ketoximes. They are more difficult to make and less stable.