An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

被引：5

作者：

Wu, Zhen ^{[1
,2
]}

Feng, Xue-Xin ^{[1
,2
]}

Wang, Qing-Dong ^{[2
]}

Liu, Xuan-Yu ^{[1
]}

Rao, Weidong ^{[3
]}

Yang, Jin-Ming ^{[1
,2
]}

Shen, Zhi-Liang ^{[1
]}

机构：

[1] Nanjing Tech Univ, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

[2] Yancheng Teachers Univ, Sch Pharm, Yancheng 224007, Peoples R China

[3] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2020年 / 31卷 / 02期

关键词：

Bismuth; Ammonium iodide; Water; Homoallylic alcohol; Diastereoselectivity; UNACTIVATED ALKYL-HALIDES; GRIGNARD-TYPE ADDITION; C-H BONDS; CARBONYL-COMPOUNDS; ORGANIC-REACTIONS; ALPHA; BETA-UNSATURATED KETONES; QUATERNARY CENTERS; IN-SITU; ORGANOINDIUM REAGENTS; ASYMMETRIC-SYNTHESIS;

D O I：

10.1016/j.cclet.2019.07.030

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate. 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：391 / 395

页数：5

共 114 条

[41] In situ generation of vinyl allenes and its applications to one-pot assembly of cyclohexene, cyclooctadiene, 3,7-nonadienone, and bicyclo[6.4.0]dodecene derivatives with palladium-catalyzed multicomponent reactions [J].

Lee, PH ;

Lee, K ;

Kang, YJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1139-1146

[42] Cyclization of 1-Bromo-2,7-and 1-Bromo-2,8-Enynes mediated by indium [J].

Lee, PH ;

Kim, S ;

Lee, K ;

Seomoon, D ;

Kim, H ;

Lee, S ;

Kim, M ;

Han, M ;

Noh, K ;

Livinghouse, T .

ORGANIC LETTERS, 2004, 6 (26) :4825-4828

[43] The Development of Catalytic Nucleophilic Additions of Terminal Alkynes in Water [J].

Li, Chao-Jun .

ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (04) :581-590

[44] Organic reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update [J].

Li, CJ .

CHEMICAL REVIEWS, 2005, 105 (08) :3095-3165

[45] Organic chemistry in water [J].

Li, CJ ;

Chen, L .

CHEMICAL SOCIETY REVIEWS, 2006, 35 (01) :68-82

[46] Quasi-nature catalysis: Developing C-C bond formations catalyzed by late transition metals in air and water [J].

Li, CJ .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (07) :533-538

[47] Novel carbocyle enlargement in aqueous medium [J].

Li, CJ ;

Chen, DL ;

Lu, YQ ;

Haberman, JX ;

Mague, JT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4216-4217

[48] ORGANIC-REACTIONS IN AQUEOUS-MEDIA - WITH A FOCUS ON CARBON-CARBON BOND FORMATION [J].

LI, CJ .

CHEMICAL REVIEWS, 1993, 93 (06) :2023-2035

[49] Electrochemical Dehydrogenative Coupling of Alcohols with Hydrogen Phosphoryl Compounds: A Green Protocol for P-O Bond Formation [J].

Li, Qian-Yu ;

Swaroop, Toreshettahally R. ;

Hou, Cheng ;

Wang, Zi-Qiang ;

Pan, Ying-Ming ;

Tang, Hai-Tao .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) :1761-1765

[50] The Bis(allyl)bismuth Cation: A Reagent for Direct Allyl Transfer by Lewis Acid Activation and Controlled Radical Polymerization [J].

Lichtenberg, Crispin ;

Pan, Fangfang ;

Spaniol, Thomas P. ;

Englert, Ulli ;

Okuda, Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (52) :13011-13015

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