Activation of carbonyl beta-carbons for chemical transformations
AssigneeNanyang Technological University
InventorsYonggui Chi, Zhenqian Fu
Life of this patent
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Abstract
The present invention relates to a method for synthesizing a compound of Formula (I) as defined herein, comprising: (i) activating a compound of Formula (II) as defined herein, by reacting said compound of Formula (II) with a compound of Formula (III) as defined herein, in the presence of a base, to obtain a compound of Formula (IV) as defined herein; and (ii) reacting the compound of Formula (IV) with an electrophile to obtain the compound of Formula (I). The present invention further relates to the organocatalysts used in the described methods and their respective uses.
Claims39
Method for synthesizing a compound of Formula (Ia)
- wherein
- n is 2;
- each R1 and R2 is independently hydrogen, halogen, —OH, —OOH, —NH2, —NO2, —ONO2, —CHO, —CN, —CNOH, —COOH, —SH, —OSH, —CSSH, —SCN, —SO2OH, —CONH2, —NH—NH2, —NC, —CSH, or any organic moiety;
- B is an electrophilic group;
- and
- NHC⊕ is
- comprising:
- (i) activating a compound of Formula (IIa)
- wherein
- LG is a leaving group;
- by reacting said compound of Formula (IIa) with a compound of Formula (III) in the presence of a base
- wherein
- R3, R4, and R5 are independently from each other hydrogen, halogen, —OH, —OOH, —NH2, —NO2, —ONO2, —CHO, —CN, —CNOH, —COOH, —SH, —OSH, —CSSH, —SCN, —SO2OH, —CONH2, —NH—NH2, —NC, —CSH, or any organic moiety;
- or
- R3 and R4 combine to form together with the atoms to which they are attached a substituted or unsubstituted 5- to 40-membered cycloalkyl, cycloalkenyl, heteroalicyclic, aryl, or heteroaryl ring, and R5 is hydrogen, halogen, —OH, —OOH, —NH2, —NO2, —ONO2, -CHO, —CN, —CNOH, —COOH, —SH, —OSH, —CSSH, -SCN, —SO2OH, —CONH2, —NH—NH2, -NC, —CSH, or any organic moiety;
- to obtain a compound of Formula (IVa)
- and
- (ii) reacting the compound of Formula (IVa) with an electrophile to obtain the compound of Formula (Ia).
Compound of Formula (VI)
- or Formula (VII)
- wherein R3, R4, R5, and R6 are independently from each other selected from the group consisting of hydrogen, halogen, —OH, —OOH, —NH2, —NO2, —ONO2, —CHO, —CN, —CNOH, —COOH, —SH, —OSH, —CSSH, —SCN, —SO2OH, —CONH2, —NH—NH2, —NC, —CSH, or any organic moiety;
- or
- R3 and R4 combine to form together with the atoms to which they are attached a substituted or unsubstituted 5- to 40-membered cycloalkyl, cycloalkenyl, heteroalicyclic, aryl, or heteroaryl ring, and R5 and R6 are independently from each other selected from the group consisting of hydrogen, halogen, —OH, —OOH, —NH2, —NO2, —ONO2, —CHO, —CN, —CNOH, —COOH, —SH, —OSH, —CSSH, -SCN, —SO2OH, —CONH2, —NH—NH2, —NC, —CSH, or any organic moiety;
- and
- X is any anion.
Dependencies are inferred from the claim text.