Oxathiaborolium: A Type of Chiral Lewis Acid Catalyst and Its Application in Catalytic and Highly Enantioselective Diels-Alder Reactions

被引：15

作者：

Kumar, Singam Naveen ^{[1
]}

Yu, Isaac Furay ^{[2
]}

Chein, Rong-Jie ^{[1
]}

机构：

[1] Acad Sinica, Inst Chem, Taipei 11529, Taiwan

[2] Natl Taiwan Univ, Dept Chem, Taipei 10617, Taiwan

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 01期

关键词：

OXAZABOROLIDINIUM ION; EFFICIENT PROCESS; CYANOSILYLATION; ACTIVATION; ALDEHYDES; PATHWAYS; BORENIUM; BROMIDE; ESTRONE; KETONES;

D O I：

10.1021/acs.orglett.6b03147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first reported sulfur-stabilized borenium cations were synthesized through halide abstraction of a haloborane intermediate by halophilic reagents. Different from the well-known cationic oxazaborolidines, a sulfide instead of an amine was used to not only simplify the preparation of the catalysts but also increase Lewis acidity of the boron atom. The in situ generated borenium salts showed exceptional Lewis acidity and successfully catalyzed asymmetric Diels-Alder reactions of cyclopentadiene and dienophiles in excellent yields and enantioselectivities. The NMR studies of these oxathiaborolium structures were reported as well.

引用

页码：22 / 25

页数：4

共 50 条

[1] A new cationic, chiral catalyst for highly enantioselective Diels-Alder reactions
Sprott, KT
Corey, EJ
[J]. ORGANIC LETTERS, 2003, 5 (14) : 2465 - 2467
[2] A CHIRAL SCANDIUM CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER REACTIONS
KOBAYASHI, S
ARAKI, M
HACHIYA, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14): : 3758 - 3759
[3] An application of electronic asymmetry to highly enantioselective catalytic Diels-Alder reactions
Faller, JW
Grimmond, BJ
D'Alliessi, DG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (11) : 2525 - 2529
[4] Design of Bronsted acid-assisted chiral Lewis acid (BLA) catalysts for highly enantioselective Diels-Alder reactions
Ishihara, K
Kurihara, H
Matsumoto, M
Yamamoto, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (28) : 6920 - 6930
[5] Design and development of highly effective lewis acid catalysts for enantioselective Diels-Alder reactions
Huang, Y
Iwama, T
Rawal, VH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) : 5950 - 5951
[6] Enantioselective Diels-Alder cycloaddition by preorganization on a chiral Lewis acid template
Bienaymé, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) : 2670 - 2673
[7] Design of chiral tin(IV) aryloxide as a mild Lewis acid catalyst for enantioselective Diels-Alder reaction
Kano, T
Konishi, T
Konishi, S
Maruoka, K
[J]. TETRAHEDRON LETTERS, 2006, 47 (06) : 873 - 875
[8] Chiral Ruthenium Lewis Acid Catalyzed Intramolecular Diels-Alder Reactions
Thamapipol, Sirinporn
Bernardinelli, Gerald
Besnard, Celine
Kuendig, E. Peter
[J]. ORGANIC LETTERS, 2010, 12 (24) : 5604 - 5607
[9] Enantioselective Diels-Alder reactions: NMR spectroscopy of a chiral titanium Lewis acid under high pressure
Tietze, LF
Ott, C
Frey, U
[J]. LIEBIGS ANNALEN, 1996, (01): : 63 - 67
[10] Oxazaborolidine-derived Lewis acid assisted Lewis acid as a moisture-tolerant catalyst for enantioselective Diels-Alder reactions
Futatsugi, K
Yamamoto, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) : 1484 - 1487

← 1 2 3 4 5 →