Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki-Miyaura Cross-Coupling

被引：36

作者：

Hoang, Gia L. ^{[1
]}

Yang, Zhao-Di ^{[1
,2
]}

Smith, Sean M. ^{[1
]}

Pal, Rhitankar ^{[3
]}

Miska, Judy L. ^{[1
]}

Perez, Damaris E. ^{[1
]}

Pelter, Libbie S. W. ^{[4
]}

Zeng, Xiao Cheng ^{[1
]}

Takacs, James M. ^{[1
]}

机构：

[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA

[2] Harbin Univ Sci & Technol, Key Lab Green Chem Engn & Technol, Coll Heilongjiang Prov, Coll Chem & Environm Engn, Harbin 150040, Peoples R China

[3] Yale Univ, Dept Chem, New Haven, CT 06518 USA

[4] Purdue Univ Calumet, Dept Chem & Phys, Hammond, IN 46323 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 04期

关键词：

HIGHLY EFFICIENT; SECONDARY; CONSTRUCTION; ARYL; MONOBORYLATION; DIBORATION; RETENTION; INVERSION; ALDEHYDES; REAGENTS;

D O I：

10.1021/ol503764d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rhodium-catalyzed enantioselective desymmetrization of symmetric gamma,delta-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral gamma-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

引用

页码：940 / 943

页数：4

共 56 条

[1] Inversion or Retention? Effects of Acidic Additives on the Stereochemical Course in Enantiospecific Suzuki-Miyaura Coupling of α-(Acetylamino)benzylboronic Esters [J].