公开(公告)号：US06559323B1

公开(公告)日：2003-05-06

申请号：US09423428

申请日：2000-02-28

Applicant: John Richard Studley ,  Varinder Kumar Aggarwal

Inventor： John Richard Studley ,  Varinder Kumar Aggarwal

IPC: C07D30102

CPC classification number: C07D303/22 ,  C07D203/02 ,  C07D301/02 ,  C07D303/04 ,  C07D303/08 ,  C07D303/46 ,  C07D327/06 ,  C07D333/54 ,  C07D333/78 ,  C07D405/04 ,  C07D495/08 ,  Y10S436/903

Abstract: A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I), wherein X is oxygen, NR4 or CHR5; R1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R2 is hydrogen, alkyl, aryl, heteroaromatic, CO2R8, CHR14NHR13, heterocyclic or cycloalkyl; or R1 and R2 join together to form a cycloalkyl ring; R3 and R10 are, independently, hydrogen, alkyl, aryl, heteroaromatic, CO2R8, R83Sn, CONR8R9, trialkylsilyl or triarylsilyl; R4 is an electron withdrawing group; R5 is alkyl, cycloalkyl, aryl, heteroaromatic, SO2R8, SO3R8, COR8, CO2R8, CONR8R9, PO(R8)2, PO(OR8)2 or CN; R8 and R9 are independently alkyl or aryl; and R13 and R14 are independently hydrogen, alkyl or aryl is provided. The process comprises degrading a compound of formula (II), (IIa), (IIb) or (IIc): wherein R3 and R10 are as defined above; Y is a cation; depending on the nature of Y, r is 1 or 2; and L is a suitable leaving group, to form a diazo compound. The diazo compound is reacted with a suitable transition metal catalyst, and the product thereof reacted with a sulphide of formula SR6R7, wherein R6 and R7 are independently alkyl, aryl or heteroaromatic, or R6 and R7 join together to form an optionally substituted ring which optionally includes an additional heteroatom. This product is then reacted with an aldehyde, ketone, imine or alkene.

Abstract translation: 制备式（I）的环氧乙烷，氮丙啶或环丙烷的方法，其中X是氧，NR 4或CHR 5; R 1是氢，烷基，芳基，杂芳族，杂环或环烷基; R2是氢，烷基，芳基，杂芳族，CO2R8，CHR14NHR13，杂环或环烷基; 或R 1和R 2连接在一起形成环烷基环; R 3和R 10独立地是氢，烷基，芳基，杂芳族，CO 2 R 8，R 83 Sn，CONR 8 R 9，三烷基甲硅烷基或三芳基甲硅烷基; R4是吸电子基团; R5是烷基，环烷基，芳基，杂芳族，SO2R8，SO3R8，COR8，CO2R8，CONR8R9，PO（R8）2，PO（OR8）2或CN; R8和R9独立地是烷基或芳基; R 13和R 14独立地为氢，提供烷基或芳基。 该方法包括降解式（II），（IIa），（IIb）或（IIc）化合物：其中R 3和R 10如上所定义; Y是阳离子; 取决于Y的性质，r为1或2; 并且L是合适的离去基团，以形成重氮化合物。 将重氮化合物与合适的过渡金属催化剂反应，其产物与式SR6R7的硫化物反应，其中R 6和R 7独立地为烷基，芳基或杂芳族，或R 6和R 7连接在一起形成任选取代的环， 包括另外的杂原子。 然后将该产物与醛，酮，亚胺或烯烃反应。

公开(公告)号：US6063920A

公开(公告)日：2000-05-16

申请号：US11010

申请日：1998-06-01

Applicant: Varinder Kumar Aggarwal

Inventor： Varinder Kumar Aggarwal

IPC: B01J31/02 ,  C07B53/00 ,  C07D223/14 ,  C07D301/03 ,  C07D301/12

CPC classification number: C07D301/12 ,  C07B53/00 ,  C07D223/14

Abstract: A compound of formula (Ia) of (Ib), wherein A and B each independently represents hydrogen or one, two or three naphthylidene substituents, which substituents are selected from C.sub.1-6 alkyl, C.sub.1-6 alkoxy, aryl, aryloxy, silyl and silyloxy; R.sup.1 represents phenyl, C.sub.1-6 alkyl, phenyl C.sub.1-6 alkyl or a moiety of formula (a): wherein R.sup.2 represents C.sub.1-6 alkyl, phenyl or benzyl, R.sup.3 represents H or OR.sup.4 wherein R.sup.4 is C.sub.1-6 alkyl or C.sub.1-6 alkylsilyl and n is zero or an integer 1 or 2; and X.sup.- is a counter ion; a process for the preparation of such compounds and the use of such compounds for enantioselectively epoxidising a prochiral olefin.

Abstract translation: PCT No.PCT / EP96 / 03551 Sec。 371日期1998年6月1日 102（e）1998年6月1日PCT PCT 1996年8月7日PCT公布。 公开号WO97 / 06147 日期：1997年2月20日（Ib）的式（Ia）化合物，其中A和B各自独立地表示氢或一个，两个或三个亚萘基取代基，该取代基选自C 1-6烷基，C 1-6烷氧基，芳基 ，芳氧基，甲硅烷基和甲硅烷氧基; R1表示苯基，C1-6烷基，苯基C1-6烷基或式（a）的部分：其中R2表示C1-6烷基，苯基或苄基，R3表示H或OR4，其中R4是C1-6烷基或C1- 6烷基甲硅烷基，n为0或1或2的整数; X-是抗衡离子; 制备这些化合物的方法以及这种化合物用于对映选择性环氧化前手性烯烃的方法。

公开(公告)号：US6114548A

公开(公告)日：2000-09-05

申请号：US8768

申请日：1998-01-19

Applicant: Christopher Paul Newman ,  Varinder Kumar Aggarwal ,  Graham Patrick Vennall

Inventor： Christopher Paul Newman ,  Varinder Kumar Aggarwal ,  Graham Patrick Vennall

IPC: B01J31/02 ,  C07B61/00 ,  C07D309/18 ,  C07D309/20 ,  C07D309/00

CPC classification number: C07D309/18 ,  C07D309/20

Abstract: The invention concerns Diels-Alder reactions between non-activated aldehydes RCHO in which R is a C1-C10 aliphatic group or phenyl group, which is unsubstituted or substituted with one or more C1-C5 alkyl groups or one other functional group, with simple aliphatic dienes R.sub.1 CH.dbd.CR.sub.2 --CR.sub.3 .dbd.CHR.sub.4 in which R.sub.1 -R.sub.4 are H or C1-C5 alkyl groups using as a catalyst a perfluorinated organic sulphonic acid or a Bronsted acid derivative thereof. The reaction leads to dihydropyrans of the structure below in which R1-R4 have the meaning indicated above.The preferred perfluorinated organic sulfonic acids are perfluorooctanesulphonic acid, triflic acid, Nafion or a Bronsted acid derivative of triflic acid. ##STR1## The preferred aldehydes are those wherein R is a C2-C6 aliphatic group or a phenyl group which is unsubstituted or mono-substituted with C1-C3 alkyl or with 4-Cl, 4-nitro or 3-methoxy. The preferred dienes are those wherein the groups R.sub.1 -R.sub.4 are H or methyl.

Abstract translation: 本发明涉及非活化醛RCHO中的Diels-Alder反应，其中R是未被取代或被一个或多个C 1 -C 5烷基或一个其它官能团取代的C 1 -C 10脂族基或苯基， 二烯R1CH = CR2-CR3 = CHR4，其中R 1 -R 4为H或C 1 -C 5烷基，使用全氟化有机磺酸或其Br + E，uml + e + nsted酸衍生物作为催化剂。 该反应得到以下结构的二氢吡喃，其中R1-R4具有上述含义。 优选的全氟化有机磺酸是全氟辛基磺酸，三氟甲磺酸，Nafion或三氟乙酸的Br + E，嗯，o + EE nsted酸衍生物。 优选的醛是其中R是C 2 -C 6脂族基团或未被取代或被C 1 -C 3烷基或与4-Cl，4-硝基或3-甲氧基单取代的苯基的那些。 优选的二烯是其中基团R 1 -R 4是H或甲基的那些。

公开(公告)号：US5703246A

公开(公告)日：1997-12-30

申请号：US617755

申请日：1996-03-15

Applicant: Varinder Kumar Aggarwal ,  Hesham Nimer Hasan Abdel-Rahman ,  Hee Yoon Lee

Inventor： Varinder Kumar Aggarwal ,  Hesham Nimer Hasan Abdel-Rahman ,  Hee Yoon Lee

IPC: C07B37/10 ,  C07B41/00 ,  C07B43/00 ,  C07C2/86 ,  C07C13/04 ,  C07C13/28 ,  C07C45/68 ,  C07C49/293 ,  C07C69/743 ,  C07C69/753 ,  C07C211/16 ,  C07C303/30 ,  C07C303/34 ,  C07C303/40 ,  C07C315/04 ,  C07D203/02 ,  C07D203/22 ,  C07D203/24 ,  C07D301/02 ,  C07D303/04 ,  C07D303/08 ,  C07D303/16 ,  C07D303/40 ,  C07D303/46 ,  C07D407/04 ,  C07F9/564 ,  C07C203/00

CPC classification number: C07D203/22 ,  C07C2/868 ,  C07D203/02 ,  C07D203/24 ,  C07D301/02 ,  C07D303/04 ,  C07D303/08 ,  C07D303/16 ,  C07D303/40 ,  C07D303/46 ,  C07D407/04 ,  C07F9/564 ,  C07C2101/02

Abstract: A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I) wherein, X is oxygen, NR.sup.4 or CHR.sup.5 ; R.sup.1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R.sup.2 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, CHR.sup.14 NHR.sup.13, heterocyclic or cycloalkyl; or R.sup.1 and R.sup.2 join together to form a cycloalkyl ring; R.sup.3 is hydrogen, alkyl, aryl, heteroaromatic, CO.sub.2 R.sup.8, R.sup.8.sub.3 Sn, CONR.sup.8 R.sup.9 or trimethylsilyl; R.sup.4 and R.sup.5 are, independently, alkyl, cycloalkyl, aryl, heteroaromatic, SO.sub.2 R.sup.8, SO.sub.3 R.sup.8, COR.sup.8, CO.sub.2 R.sup.8, CONR.sup.8 R.sup.9 or CN, or R.sup.4 can also be P(O)(aryl).sub.2 ; R.sup.8 and R.sup.9 are independently alkyl, aryl or arylalkyl; R.sup.13 and R.sup.14 are independently hydrogen, alkyl or aryl; the process comprising reacting a mixture of a compound of formula (II), wherein R.sup.1, R.sup.2 and X are as defined above, and a sulphide of formula SR.sup.6 R.sup.7, wherein R.sup.6 and R.sup.7 are independently alkyl, aryl or heteroaomatic, or R.sup.6 and R.sup.7 join together to form a cycloalkyl ring which optionally includes an additional heteroatom, with either (i) a metallocarbon obtainable by reacting an alkylmetal with a methane derivative of formula CHR.sup.3 X'X", wherein R.sup.3 is as defined above, and X' and X" are independently, a leaving group, or (ii) a metallocarbon obtainable by reacting a compound of formula (III), (wherein R.sup.3 may not be hydrogen) with a suitable organometallic or inorganic reagent.

Abstract translation: PCT No.PCT / GB94 / 02280第 371日期：1996年3月15日 102（e）1996年3月15日PCT 1994年10月19日PCT PCT。 公开号WO95 / 11230 日期：1995年04月27日制备式（I）的环氧乙烷，氮丙啶或环丙烷的方法，其中X是氧，NR 4或CHR 5; R 1是氢，烷基，芳基，杂芳族，杂环或环烷基; R2是氢，烷基，芳基，杂芳族，CO2R8，CHR14NHR13，杂环或环烷基; 或R 1和R 2连接在一起形成环烷基环; R3是氢，烷基，芳基，杂芳族，CO2R8，R83Sn，CONR8R9或三甲基甲硅烷基; R4和R5独立地是烷基，环烷基，芳基，杂芳族，SO2R8，SO3R8，COR8，CO2R8，CONR8R9或CN，或R4也可以是P（O）（芳基）2; R8和R9独立地是烷基，芳基或芳基烷基; R 13和R 14独立地是氢，烷基或芳基; 该方法包括使式（II）化合物（其中R 1，R 2和X如上所定义）和式SR 6 R 7的硫化物的混合物反应，其中R 6和R 7独立地为烷基，芳基或杂芳基，或R 6和R 7连接 一起形成任选地包括另外的杂原子的环烷基环，与（i）通过使烷基金属与式CHR 3 X'X“的甲烷衍生物反应得到的金属碳，其中R 3如上所定义，X'和X' 独立地是离去基团，或（ii）可通过使式（III）化合物（其中R 3可以不是氢）与合适的有机金属或无机试剂反应得到的金属碳。