PMID: 11925225Apr 2, 2002Paper

A highly enantioselective hetero-Diels-Alder reaction of aldehydes with Danishefsky's diene catalyzed by chiral titanium(IV) 5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol complexes

The Journal of Organic Chemistry
Bin WangYaozhong Jiang

Abstract

The catalytic effect of chiral Lewis acids on the hetero-Diels-Alder reaction between aldehydes and Danishefsky's diene (1) has been investigated. A variety of combinations of different ligands and Lewis acids have been examined as catalysts for the hetero-Diels-Alder reaction between benzaldehyde and 1, and it has been found that the readily accessible Ti(IV)-H(8)-BINOL (TiHBOL) complex is a very effective catalyst for the reaction, leading to products with very high enantioselectivity (up to 99% ee) and yield (92%). The hetero-Diels-Alder reaction of other aldehydes with 1 under the catalysis of TiHBOL is a general reaction which proceeds well with very high enantioselectivity and isolated yield for various aldehydes at 0 degrees C to room temperature. Based on the experimental results, the proposed mechanism of the hetero-Diels-Alder reaction and the dihedral angle effects of ligands are discussed.

Citations

Sep 16, 2009·Chemical Communications : Chem Comm·Xiaochen WangMichael P Doyle
Apr 3, 2004·Proceedings of the National Academy of Sciences of the United States of America·Michael P DoylePenglin Huang
Apr 10, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hannah J EdwardsChristopher G Frost
Sep 12, 2019·Chemistry, an Asian Journal·Anand Yadav, Prakash Kanoo
May 17, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Mingsheng XieXiaoming Feng
May 21, 2008·The Journal of Organic Chemistry·Lars V Heumann, Gary E Keck
Jan 28, 2009·The Journal of Organic Chemistry·Xinsheng LiDongcheng Xu
Nov 26, 2014·Chemical Reviews·Bagher Eftekhari-Sis, Maryam Zirak

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