Preparation of Bicyclic Ketal Skeletons with Aldehyde and α-Ketone Acid through Cascade Friedel-Crafts Reaction and Stereoselective Acetalization in One Pot

被引：0

作者：

Li, Ling ^{[1
]}

Wang, Ying-wei ^{[1
]}

Zhang, Shi-qi ^{[1
]}

Dong, Xiong-fei ^{[1
]}

Li, Guang-xun ^{[2
]}

Zhao, Gang ^{[1
]}

Tang, Zhuo ^{[2
]}

机构：

[1] Sichuan Univ, Coll Chem Engn, Chengdu 610041, Sichuan, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Sichuan, Peoples R China

来源：

SYNLETT | 2019年 / 30卷 / 18期

关键词：

bicyclic ketal skeletons; Friedel-Crafts reaction; tandem reaction; alpha-ketone acid; Bronsted acid; acetalization; RHODIUM CARBENOIDS; CARBONYL-COMPOUNDS; SINGLET OXYGEN; TANDEM; PRODUCTS;

D O I：

10.1055/s-0039-1690696

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic ketal skeletons are important structure fragments that are frequently contained in natural products. A novel tandem Friedel-Crafts reaction and subsequent stereoselective acetalization were developed with readily available aldehyde and ketone acid. The reaction proceeded smoothly in the presence of catalytic Bronsted acid and afforded the corresponding product with moderate yield and high stereoselectivity.

引用

页码：2091 / 2095

页数：5

共 28 条

[1] Intermolecular reactions of chlorohydrine anions: Acetalization of carbonyl compounds under basic conditions [J].

Barbasiewicz, Michal ;

Makosza, Mieczyslaw .

ORGANIC LETTERS, 2006, 8 (17) :3745-3748

[2] Simple, rapid procedure for the synthesis of chloromethyl methyl ether and other chloro alkyl ethers [J].

Berliner, MA ;

Belecki, K .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9618-9621

[3] Chiral Phosphoric-Acid-Catalyzed Regioselective and Enantioselective C7-Friedel-Crafts Alkylation of 4-Aminoindoles with Trifluoromethyl Ketones [J].

Cai, Lu ;

Zhao, Yunlong ;

Huang, Tongkun ;

Meng, Shanshui ;

Jia, Xian ;

Chan, Albert S. C. ;

Zhao, Junling .

ORGANIC LETTERS, 2019, 21 (10) :3538-3542

[4] One-Pot Conversion of Thebaine to Hydrocodone and Synthesis of Neopinone Ketal [J].

Carroll, Robert J. ;

Leisch, Hannes ;

Rochon, Lena ;

Hudlicky, Tomas ;

Cox, D. Phillip .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) :747-752

[5]

CITTERIO A, 1984, SYNTHESIS-STUTTGART, P760

[6] Glycosylation Catalyzed by a Chiral Bronsted Acid [J].

Cox, Daniel J. ;

Smith, Martin D. ;

Fairbanks, Antony J. .

ORGANIC LETTERS, 2010, 12 (07) :1452-1455

[7]

Firouzabadi H, 1999, SYNLETT, P321

[8] Intramolecular hydrogen abstraction reaction promoted by alkoxy radicals in carbohydrates.: Synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane and 6,8-dioxabicyclo[3.2.1]octane ring systems [J].

Francisco, CG ;

Herrera, AJ ;

Suárez, E .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7439-7445

[9] Preparation of acetals from aldehydes and alcohols under basic conditions [J].

Grabowski, Jakub ;

Granda, Jaroslaw M. ;

Jurczak, Janusz .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (17) :3114-3120

[10] STEREOSELECTIVE ACETALIZATION OF 1,3-ALKANEDIOLS CONTROLLED BY INTRAMOLECULAR VAN-DER-WAALS ATTRACTIVE INTERACTIONS AND ITS APPLICATION TO AN ENANTIODIFFERENTIATING TRANSFORMATION OF SIGMA-SYMMETRICAL 1,3,5-PENTANETRIOLS [J].

HARADA, T ;

INOUE, A ;

WADA, I ;

UCHIMURA, JJ ;

TANAKA, S ;

OKU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (17) :7665-7674

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