Nobuyuki Kawai

Name:

Organization: Kyoto Pharmaceutical University

Department:

Title:

Chemicals
References

Stereoselective synthesis of contiguous THF–THF and THF–THP units via PdII-catalyzed tandem reaction with 1,3-chirality transfer

Co-reporter:Nobuyuki Kawai, Yuhei Fujikura, Jun Takita, Jun'ichi Uenishi

Tetrahedron 2013 69(51) pp: 11017-11024

Publication Date(Web):

DOI:10.1016/j.tet.2013.09.067

Stereoselective synthesis of tetrahydroisoquinoline alkaloids: (−)-trolline, (+)-crispin A, (+)-oleracein E

Co-reporter:Nobuyuki Kawai, Mika Matsuda, Jun’ichi Uenishi

Tetrahedron 2011 67(45) pp: 8648-8653

Publication Date(Web):

DOI:10.1016/j.tet.2011.09.033

Synthesis of Chiral 1-Substituted Tetrahydroisoquinolines by the Intramolecular 1,3-Chirality Transfer Reaction Catalyzed by Bi(OTf)3

Co-reporter:Nobuyuki Kawai, Ryuzou Abe, Mika Matsuda, and Jun’ichi Uenishi

The Journal of Organic Chemistry 2011 Volume 76(Issue 7) pp:2102-2114

Publication Date(Web):February 28, 2011

DOI:10.1021/jo102452d

The intramolecular 1,3-chirality transfer reaction of chiral amino alcohols 1 with 99% ee was developed to construct chiral 1-substituted tetrahydroisoquinoline 2. Bi(OTf)3 (10 mol %)-catalyzed cyclization of 1 (R = H) afforded (S)-1-(E)-propenyl tetrahydroisoquinoline 2 (R = H) in 83% yield with a ratio of 98:2. The stereochemistry at the newly formed chiral center was produced by a syn SN2′-type process. In this reaction, the substituent on the benzene ring of 1 significantly affected the reactivities and selectivities. A plausible reaction mechanism was proposed.

Lewis acid-catalyzed intramolecular amination via 1,3-chirality transfer

Co-reporter:Nobuyuki Kawai, Ryuzou Abe, Jun’ichi Uenishi

Tetrahedron Letters 2009 50(47) pp: 6580-6583

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.09.053

Stereochemistry and Construction of Tetrasubstituted Chiral Carbon Centers in Intramolecular Pd-Catalyzed 1,3-Chirality Transfer Reactions

Co-reporter:Jean-Marie Lagrange;Jun'ichi Uenishi

European Journal of Organic Chemistry 2007 Volume 2007(Issue 17) pp:2808-2814

Publication Date(Web):12 APR 2007

DOI:10.1002/ejoc.200601103

A Pd^II-catalyzed cyclization for the construction – from chiral allylic alcohols – of tetrahydropyrans containing tetrasubstituted chiral carbons proceeded stereospecifically by 1,3-chirality transfer through a syn-S_N2′ type process. The chiral 2,2,6-trisubstituted tetrahydropyrans 5 and spiro hydropyrans 6 were obtained in high yields under mild reaction conditions.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)