An efficient double 1,2-addition reaction of 2,3-allenoates with allyl magnesium chloride.
作者： Bo Chen , Zhan Lu , Guobi Chai , Chunling Fu , Shengming Ma
DOI: 10.1021/JO801809J
关键词: Chemistry 、 Polymer chemistry 、 Organic chemistry 、 Chemical synthesis 、 Racemization 、 Catalysis 、 Magnesium 、 Addition reaction 、 Axial chirality 、 Transition metal 、 Chirality (chemistry)
摘要: In this paper, it was reported that double 1,2-addition reaction of 2,3-allenoates with allyl magnesium chloride at room temperature in the absence any transition metal catalyst provides an efficient method for synthesis tertiary α-allenols. The optically active allenol could be prepared from 2,3-allenoate without obvious racemization axial chirality. Under different conditions, cyclization reactions α-allenol 2i have been studied 2,5-dihydrofuran derivatives.
acs.org
sci-hub.se 参考文章(47)
Modern Allene Chemistry Wiley-VCH Verlag GmbH. ,(2004) , 10.1002/9783527619573
Benito Alcaide, Pedro Almendros, Raquel Rodríguez-Acebes, Pd–Cu Bimetallic Catalyzed Domino Cyclization of α‐Allenols Followed by a Coupling Reaction: New Sequence Leading to Functionalized Spirolactams Chemistry: A European Journal. ,vol. 11, pp. 5708- 5712 ,(2005) , 10.1002/CHEM.200500228
Anja Hoffmann-Röder, Norbert Krause, Gold(III) Chloride Catalyzed Cyclization of α-Hydroxyallenes to 2,5-Dihydrofurans Organic Letters. ,vol. 3, pp. 2537- 2538 ,(2001) , 10.1021/OL016205+
Shengming Ma, Zhenhua Gu, PdCl2-catalyzed two-component cross-coupling cyclization of 2,3-allenoic acids with 2,3-allenols. An efficient synthesis of 4-(1',3'-dien-2'-yl)-2(5H)-furanone derivatives. Journal of the American Chemical Society. ,vol. 127, pp. 6182- 6183 ,(2005) , 10.1021/JA0500815
Zhan Lu, Guobi Chai, Xiaobing Zhang, Shengming Ma, Controllable highly stereoselective reaction of in situ generated magnesium dienolate intermediates with different electrophiles. Organic Letters. ,vol. 10, pp. 3517- 3520 ,(2008) , 10.1021/OL8012815
Sham S. Nikam, Kai Hsuan Chu, Kung K. Wang, Cyclization of trimethylsilyl-substituted α-allenic alcohols to 3-(trimethylsilyl)-2,5-dihydrofurans and their facile autoxidation to 3-(trimethylsilyl)furans or 4-(trimethylsilyl)-2(5H)-furanones Journal of Organic Chemistry. ,vol. 51, pp. 745- 747 ,(1986) , 10.1021/JO00355A034
Youqian Deng, Yihua Yu, Shengming Ma, PdCl2/NaI-catalyzed homodimeric coupling-cyclization reaction of 2,3-allenols: an efficient synthesis of 4-(1',3'-dien-2'-yl)-2,5-dihydrofuran derivatives. Journal of Organic Chemistry. ,vol. 73, pp. 585- 589 ,(2008) , 10.1021/JO702332M
James A. Marshall, Xiao Jun Wang, Synthesis of enantioenriched .alpha.-hydroxy-.alpha.-allenylacetic acids by [2,3] Wittig rearrangement of .alpha.-(propargyloxy)acetates Journal of Organic Chemistry. ,vol. 56, pp. 4913- 4918 ,(1991) , 10.1021/JO00016A020
G Buono, Nouvelle voie d'acces aux cetones, esters, nitriles α- alleniques Tetrahedron Letters. ,vol. 13, pp. 3257- 3259 ,(1972) , 10.1016/S0040-4039(01)94017-1
Reinhold Zimmer, Chimmanamada U. Dinesh, Erathodiyil Nandanan, Faiz Ahmed Khan, Palladium-Catalyzed Reactions of Allenes† Chemical Reviews. ,vol. 100, pp. 3067- 3126 ,(2000) , 10.1021/CR9902796