Journal of Organic Chemistry p. 6025 - 6031 (1995)
Update date:2022-08-03
Topics:
Olsen, Richard K.
Feng, Xianqi
Campbell, Magnus
Shao, Rui-lian
Math, Shivanand K.
The Diels-Alder reaction involving cycloaddition of aryloxy-substituted 1,3-butadienes with appropriate acetylenic electrophiles, followed by aromatization of the newly formed cyclohexadiene ring, has been used for the synthesis of diaryl ethers.The functionalized aryloxy 1,3-butadienes employed in this study were prepared by either of two methods: (1) methylenation of aryl esters via the Tebbe or related reagents, and (2) from 1-(aryloxy)-2-propanone by a sequence of formylation or alkylthio methylenation, and subsequent enolsilylation.A tetrasubstituted butadiene containing two phenoxy groups at the 1 and 3 positions also was prepared by the latter method.The cycloaddition reactions of 2,3-dioxy-substituted dienes occurred in high yield, but, as expected, with no regioselectivity to furnish nearly equal mixtures of regioisomeric cycloadducts.In contrast, application of 1,2,3-trihetero-substituted dienes resulted in regiospecific cycloaddition reactions.Transformation of the cyclohexadiene cycloadducts to an aromatic ring was accomplished by dehydrogenation with DDQ or by elimination during the cycloaddition process of a molecule of an alkyl mercaptan.A chiral acetylenic ketone derived from D- or L-serine underwent condensation, without racemization, with aryloxy dienes to provide diaryl ethers related to the isodityrosine antibiotics.
View MoreContact:86-791-86629460
Address:1-6F, 118 Xinzhou road, Nanchang, Jiangxi, China
Jinan Yijialian Economic and Trade Development Co., Ltd.
Contact:+86 0531-66729596
Address:jinan
Beijing Wisdom Chemicals Co., Ltd.
Contact:+86-10-52350335
Address:F2, BLDG 19, Liando Valley U, Majuqiao, Tongzhou District, Beijing, China
Shanghai Balmxy Pharmaceutical Co., Ltd
Contact:0086-21-24206007
Address:Room 402, 15#, No. 909 wangyue Road, shanghai, P. R. China
Tianjin Chemsyntech Chemical Co., Ltd
Contact:+86-22-60872258
Address:Haitai green industry base in Tianjin, K1,5-601
Doi:10.1016/j.tetlet.2010.08.106
(2010)Doi:10.1016/0009-3084(95)02486-3
(1995)Doi:10.1002/jhet.5570380239
(2001)Doi:10.1016/j.bioorg.2019.103539
(2020)Doi:10.1016/j.tet.2018.10.071
(2018)Doi:10.1021/ja00156a010
(1995)