Carbohydrates as enantioinduction components in stereoselective catalysis

被引：29

作者：

Henderson, Alexander S. ^{[1
]}

Bower, John F. ^{[1
]}

Galan, M. Carmen ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Cantocks Close, Bristol BS8 1TS, Avon, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

N-HETEROCYCLIC CARBENES; ENANTIOSELECTIVE ALLYLIC SUBSTITUTION; ASYMMETRIC TRANSFER HYDROGENATION; CHIRAL BIS(OXAZOLINE) LIGANDS; D-GLUCOSE; STRECKER REACTION; PHOSPHITE-OXAZOLINES; HIGHLY VERSATILE; MANNICH REACTION; RECENT PROGRESS;

D O I：

10.1039/c6ob00368k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbohydrate derivatives are readily available chiral molecules, yet they are infrequently employed as enantioinduction components in stereoselective catalysis. In this review, synthetic approaches to carbohydrate-based ligands and catalysts are outlined, along with example applications in enantioselective catalysis. A wide range of carbohydrate-based functionality is covered, and key trends and future opportunities are identified.

引用

页码：4008 / 4017

页数：10

共 119 条

[1] A new P,S-Chiral auxiliary derived from thioglucose. X-ray structure of a palladium 1,3-diphenylallyl complex with a strongly rotated allyl ligand [J].

Albinati, A ;

Pregosin, PS ;

Wick, K .

ORGANOMETALLICS, 1996, 15 (10) :2419-2421

[2] Heteroarylboronates in Rhodium-Catalyzed 1,4-Addition to Enones [J].

Albrecht, Fabian ;

Sowada, Oliver ;

Fistikci, Meryem ;

Boysen, Mike M. K. .

ORGANIC LETTERS, 2014, 16 (19) :5212-5215

[3] Enantioselective catalysis using phosphorus-donor ligands containing two or three P-N or P-O bonds [J].

Ansell, J ;

Wills, M .

CHEMICAL SOCIETY REVIEWS, 2002, 31 (05) :259-268

[4] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[5] 2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination [J].

Assalit, Aurelie ;

Billard, Thierry ;

Chambert, Stephane ;

Langlois, Bernard R. ;

Queneau, Yves ;

Coe, Diane .

TETRAHEDRON-ASYMMETRY, 2009, 20 (05) :593-601

[6] Recent Developments in the Application of Organocatalysis to Glycosylations [J].

Balmond, Edward I. ;

Galan, M. Carmen ;

McGarrigle, Eoghan M. .

SYNLETT, 2013, 24 (18) :2335-2339

[7] Enantioselective organocatalysis of strecker and Mannich reactions based on carbohydrates [J].

Becker, Christian ;

Hoben, Christine ;

Kunz, Horst .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :417-424

[8] Rational design of pseudo-enantiomeric libraries of ligands based on pyranoses for application in asymmetric catalysis [J].

Benessere, Vincenzo ;

Lega, Matteo ;

Ruffo, Francesco .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 771 :105-116

[9] Carbohydrates as building blocks of privileged ligands [J].

Benessere, Vincenzo ;

Del Litto, Raffaella ;

De Roma, Antonella ;

Ruffo, Francesco .

COORDINATION CHEMISTRY REVIEWS, 2010, 254 (5-6) :390-401

[10] New chiral N,S-ligands based on oxazoline-thioglucose donors. Palladium(II)-catalyzed enantioselective allylic alkylation [J].

Boog-Wick, K ;

Pregosin, PS ;

Trabesinger, G .

ORGANOMETALLICS, 1998, 17 (15) :3254-3264

← 1 2 3 4 5 6 7 8 9 10 →