Chiral spirocyclic compounds and methods of preparation and use thereof
AssigneeThe Hong Kong University of Science and Technology
InventorsJianwei SUN, Ronghua ZHANG, Jingyi WANG, Youshao TU, Chenxiao QIAN, Qiang DAI, Yu BAO
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Abstract
Spirocyclic compounds, including chiral spiro diamine, chiral spiro amino naphthol, chiral spiro bis(indole), chiral spiro diaryl diol, chiral spiro diaryl diamine, chiral spiro amino naphthol, chiral spiro diaryl diindole, and chiral spiro phospholane useful as chiral ligands and chiral organocatalysts and methods of preparation and methods of use thereof. Owing to the molecular shape and three-dimensional orientation, the chiral diamine and chiral amino naphthol molecules provide a skeleton for use as ligands and organocatalysts.
Claims20
A compound of Formula 1, 2, 3, or 4:
- or a conjugate salt thereof, wherein:
- A is —(CR2)n—, wherein n for each instance is independently a whole number selected from 1-5 and R for each instance is independently hydrogen, alkyl, cycloalkyl, aryl, aralkyl, or a covalent bond to Z;
- each B is independently —CH2OR20, —CH2NR202, —OR20, —NR202, —PR202, —OP(OR20)2, —NHPR202, —NHP(OR20)2, —NH(C═S)NHR20, or a moiety represented by:
- or
- two instances of B taken together form a moiety having a structure selected from the group consisting of:
- each Y is independently selected from the group consisting of:
- —O—, —S—, —(NR20)—, and —(NPR202)—;
- Z is —(CR2)n—, wherein n for each instance is independently a whole number selected from 1-5 and R for each instance is independently hydrogen, alkyl, cycloalkyl, aryl, or aralkyl;
- each of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aralkyl, aryl, heteroaryl, halide, trialkylsilane, and triarylsilane;
- or
- each of R7 and R8 is independently —CH2OR20, —CH2NR202, —OR20, —NR202, —PR202, —OP(OR20)2, —NHPR202, —NHP(OR20)2, or a moiety represented by:
- or
- R7 and R8 is taken together form a moiety having a structure selected from the group consisting of:
- each of R13 and R14 is independently, hydrogen, alkyl, cycloalkyl, aryl, or aralkyl;
- and
- R20 for each instance is independently hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, heteroaryl, or —CHPhCH2PPh2;
- or two instances of R20 taken together form 5-7 membered heterocyclic group.
Dependencies are inferred from the claim text.