Nanyang Technological University

Jian Xiao

Teck Peng Loh

The present invention relates to a compound of general Formula (VIII), the compound having a bowl-shaped conformation, its formation and its use in asymmetric catalysis. In Formula (VIII), M is a metal selected from the group consisting of Group 1 to Group 14 metals, lanthanides and actinides; R is one of &#x2014;COOR, &#x2014;RCOOR, &#x2014;RCHO, &#x2014;RCOR, &#x2014;RCONRR, &#x2014;RCOX, &#x2014;ROP(&#x2550;O)(OH), &#x2014;RP(&#x2550;O)(OH)), &#x2014;RC(O)C(R)CRRand RCOC(R)O, wherein R, R, R, R, Rand Rare as defined herein.

Tricyclic chiral compounds and their use in asymmetric catalysis

The present invention relates to a compound of general Formula (XX), its formation and its use in asymmetric catalysis. In Formula (XX) R and Rare independently &#x2014;COOR, &#x2014;RCOOR, &#x2014;RCHO, &#x2014;RCOR, &#x2014;RCONRR, &#x2014;RCOX, &#x2014;ROP(&#x2550;O)(OH), &#x2014;RP(&#x2550;O)(OH)), &#x2014;RC(O)C(R)CRRand &#x2014;RCOCOR. In addition, Rmay also be hydrogen. R, Rand Rare independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. Ran aliphatic bridge with a main chain having 1 to about 20 carbon atoms, an alicyclic bridge, an aromatic bridge, an arylaliphatic bridge or an arylalicyclic bridge, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si, and X is halogen. In Formula (XX) Ris &#x2014;C(OH)RRor &#x2014;COOR, wherein R, Rand Rare independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si.

The present invention relates to an octahydro biquinoline compound. Provided is also a method of separating the octahydro biquinoline compound into enantiomers. The octahydro biquinoline compound is of the general formula (V): In formula (V) Ris one of H, a protective group and an aliphatic group, with the aliphatic group having a main chain of a length of 1 to about 10 carbon atoms, comprising 0 to about 6 heteroatoms selected from the group consisting of N, O, S, Se and Si. Rand Rare independent from one another selected from the group consisting of (i) H, (ii) one of an aliphatic, an alicyclic, an aromatic, an arylaliphatic, and an arylalicyclic group comprising 0 to about 6 heteroatoms selected from the group consisting of N, O, S, Se and Si, an ester, a carbonate group, a carbamoyl group and a phosphate ester. Rand Rare independent from one another H, an aliphatic, an alicyclic, an aromatic, an arylaliphatic or an arylalicyclic group comprising 0 to about 6 heteroatoms selected from the group consisting of N, O, S, Se and Si.

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Singapore, Singapore

Jian Xiao