Diastereoselective synthesis of arylglycine derivatives by cationic Palladium(II)-Catalyzed addition of arylboronic acids to N-tert-Butanesulfinyl imino esters

被引：87

作者：

Dai, Huixiong ^{[1
]}

Lu, Xiyan ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 16期

关键词：

D O I：

10.1021/ol0711220

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A cationic palladium-complex-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl iminoacetates to yield the optically active arylglycine derivatives with moderate to good yield and high diastereoselectivity was developed. This reaction provides a convenient and efficient method for the synthesis of arylglycine derivatives.

引用

页码：3077 / 3080

页数：4

共 37 条

[21]

Meijere A., 2004, METAL CATALYZED CROS

[22]

Mikami K, 2005, TOP ORGANOMETAL CHEM, V14, P279

[23]

Miura M, 2002, TOP CURR CHEM, V219, P211

[24] Catalytic asymmetric allylation of imines via chiral bis-π-allylpalladium complexes [J].

Nakamura, H ;

Nakamura, K ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (17) :4242-4243

[25] 1,4-addition of axylboronic acids and arylsiloxanes to α,β-unsaturated carbonyl compounds via transmetalation to dicationic palladium(II) complexes [J].

Nishikata, T ;

Yamamoto, Y ;

Miyaura, N .

ORGANOMETALLICS, 2004, 23 (18) :4317-4324

[26] C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines [J].

Otomaru, Y ;

Tokunaga, N ;

Shintani, R ;

Hayashi, T .

ORGANIC LETTERS, 2005, 7 (02) :307-310

[27] Palladium-catalyzed allylation of imines with allyl alcohols [J].

Shimizu, M ;

Kimura, M ;

Watanabe, T ;

Tamaru, Y .

ORGANIC LETTERS, 2005, 7 (04) :637-640

[28] Palladium pincer-complex catalyzed allylation of tosylimines by potassium trifluoro(allyl)borates [J].

Solin, N ;

Wallner, OA ;

Szabó, KJ .

ORGANIC LETTERS, 2005, 7 (04) :689-691

[29]

Tamaru Y., 2002, HDB ORGANOPALLADIUM, V2, P1917

[30] C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands:: Their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines [J].

Tokunaga, N ;

Otomaru, Y ;

Okamoto, K ;

Ueyama, K ;

Shintani, R ;

Hayashi, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13584-13585

← 1 2 3 4 →