Process for preparing heterocyclic (R)- and (S)-cyanohydrins
    10.
    发明授权
    Process for preparing heterocyclic (R)- and (S)-cyanohydrins 失效
    制备杂环(R) - 和(S) - 氰基醇的方法

    公开(公告)号:US07052885B2

    公开(公告)日:2006-05-30

    申请号:US10325922

    申请日:2002-12-23

    摘要: A process for preparing enantiomer-enriched heterocyclic (R)- and (S)-cyanohydrins of the formula (I), where R1, R2, R3, R4 independently of one another are H, an unsubstituted or substituted C1–C24-alkyl, alkenyl or alkynyl radical, where one or more carbon atoms in the chain can be replaced by an oxygen atom, a nitrogen atom, a sulfur atom, an SO or an SO2 group, an unsubstituted or substituted aryl or heteroaryl radical or heterocyclic radical or halogen, hydroxyl, NR5R6, acetyl, oxo, C1–C6-carbalkoxy, C1–C6-carbalkoxyamino, COOR7, cyano, amide, benzoylamino or NO2,R5 and R6 are H, C1–C6-alkyl radical, phenyl radical, benzyl radical or COOR7, or together form a C2–C8-alkylene or heteroalkylene radical,R7 is H or C1–C6-alkyl,n is 0, 1, 2 or 3,X, Y and Z can be an unsubstituted or substituted carbon atom or a radical selected from the group consisting of N, O, S or NR5R6, where R5 and R6 are as defined above, SO or SO2, and at least one of the radicals X, Y and Z is not a carbon atom, where the compounds of the formula (I) can have one or more double bonds in the ring, with the proviso that in a 5-membered ring the double bond is not conjugated with the —C(OH)CN-group, and/or can be anellated and/or bridged,by reacting a ketone of the formula (II), where R1, R2, R3, R4, X, Y, Z and n have the meanings above, with an (R)- or (S)-hydroxynitrile lyase in an organic, aqueous or two-phase system, or in emulsion, in the presence of a cyanide group donor.

    摘要翻译: 制备式(I)的对映异构体富集的杂环(R) - 和(S) - 氰基醇的方法,其中R 1,R 2,R 3,R 4彼此独立地是H,未取代或取代的C 1 - 链烯基或炔基,其中链中的一个或多个碳原子可以被氧原子,氮原子,硫原子,SO或 SO 2 2基团,未取代或取代的芳基或杂芳基或杂环基或卤素,羟基,NR 5 R 6,乙酰基,氧代C 1 -C 6 - 亚烷基氧基,C 1 -C 6 - 烷氧基氨基,COOR 7,氰基,酰胺,苯甲酰氨基或NO 2,R 5和R 6是H C 1 -C 6 - 烷基,苯基,苄基或COOR 7,或一起形成C 1 -C 6 - 8亚烷基或杂亚烷基,R 7是H或C 1 -C 6 - 烷基,n是0,1,2或3,X,Y 并且Z可以是未取代或取代的碳原子或选自它的基团 由N,O,S或NR5R6组成的基团,其中R 5和R 6如上定义,SO或SO 2,并且基团X,Y和Z中的至少一个不是碳 原子,其中式(I)的化合物可以在环中具有一个或多个双键,条件是在5元环中双键不与-C(OH)CN-基团共轭,并且 /或可以通过使式(II)的酮(其中R 1,R 2,R 3,R 4,X,Y,Z和n具有上述含义)与(R) - 或( S) - 羟基腈裂解酶在有机,水相或两相体系中,或在乳液中,在氰化物基团给体存在下。