β-isocupreidine-catalyzed baylis -: Hillman reaction of chiral N-boc-α-amino aldehydes

被引：69

作者：

Nakano, Ayako ^{[1
]}

Takahashi, Keisuke ^{[1
]}

Ishihara, Jun ^{[1
]}

Hatakeyama, Susumi ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 23期

关键词：

D O I：

10.1021/ol0622561

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] beta-Isocupreidine (beta-ICD)-catalyzed Baylis-Hillman reaction of chiral N-Boc-alpha-amino aldehydes and 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) takes place without racemization and exhibits the match-mismatch relationship between the substrate and the catalyst. In the case of acyclic amino aldehydes, L-substrates show excellent syn selectivity and high reactivity in contrast to D-substrates. On the other hand, in the case of cyclic amino aldehydes, D-substrates rather than L-substrates show excellent anti selectivity and high reactivity.

引用

页码：5357 / 5360

页数：4

共 28 条

[1] Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis
Aggarwal, VK
Fulford, SY
Lloyd-Jones, GC
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) : 1706 - 1708
[2] An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis-Hillman reaction
Almeida, WP
Coelho, F
[J]. TETRAHEDRON LETTERS, 2003, 44 (05) : 937 - 940
[3] AMEER F, 1986, S AFR J CHEM, V39, P57
[4] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
Basavaiah, D
Rao, PD
Hyma, RS
[J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
[5] Recent advances in the Baylis-Hillman reaction and applications
Basavaiah, D
Rao, AJ
Satyanarayana, T
[J]. CHEMICAL REVIEWS, 2003, 103 (03) : 811 - 891
[6] Bifunctional activation and racemization in the catalytic asymmetric aza-Baylis-Hillman reaction
Buskens, P
Klankermayer, J
Leitner, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (48) : 16762 - 16763
[7] Campbell AD, 1998, SYNTHESIS-STUTTGART, P1707
[8] Ciganek E., 1997, ORG REACTIONS, V51, P201
[9] The Baylis-Hillman reaction with chiral α-amino aldehydes under racemization-free conditions
Coelho, F
Diaz, G
Abella, CAM
Almeida, WP
[J]. SYNLETT, 2006, (03) : 435 - 439
[10] STEREOCHEMISTRY ASSOCIATED WITH THE ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO DIFFERENTIALLY PROTECTED ALPHA-AMINO ALDEHYDES - APPLICATIONS TOWARD THE SYNTHESIS OF AMINO-SUGARS AND SPHINGOSINES
DONDONI, A
FANTIN, G
FOGAGNOLO, M
PEDRINI, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) : 1439 - 1446

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