Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters

被引：121

作者：

Beenen, Melissa A. ^{[1
]}

Weix, Daniel J. ^{[1
]}

Ellman, Jonathan A. ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 19期

关键词：

D O I：

10.1021/ja060529h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new method for the Rh(I)-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters has been developed for the asymmetric synthesis of arylglycine derivatives. This method provides high yields (61-90%) and diastereoselectivities (>98:2) for a variety of functionalized arylboronic acids. The N-sulfinyl arylglycine ester products are versatile intermediates for further transformations, including selective protecting group removal, conversion to β-amino alcohols, and direct incorporation into peptides. Copyright © 2006 American Chemical Society.

引用

页码：6304 / 6305

页数：2

共 26 条

[1] A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines [J].

Bolshan, Y ;

Batey, RA .

ORGANIC LETTERS, 2005, 7 (08) :1481-1484

[2] 1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].

CARPINO, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398

[3] Concise asymmetric synthesis of α-amino acid derivatives from N-sulfinylimino esters [J].

Davis, FA ;

McCoull, W .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3396-3397

[4] Bifunctional lewis acid-nucleophile-based asymmetric catalysis:: Mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of β-lactams [J].

France, S ;

Shah, MH ;

Weatherwax, A ;

Wack, H ;

Roth, JP ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1206-1215

[5] Clopidogrel - A review of its use in the prevention of atherothrombosis [J].

Jarvis, B ;

Simpson, K .

DRUGS, 2000, 60 (02) :347-377

[6] Asymmetric synthesis and translational competence of L-α-(1-cyclobutenyl)glycine [J].

Jayathilaka, LP ;

Deb, M ;

Standaert, RF .

ORGANIC LETTERS, 2004, 6 (21) :3659-3662

[7]

Kjærsgaard A, 2005, ORG BIOMOL CHEM, V3, P804

[8] Catalytic, asymmetric Mannich-type reactions of N-acylimino esters:: Reactivity, diastereo- and enantioselectivity, and application to synthesis of N-acylated amino acid derivatives [J].

Kobayashi, S ;

Matsubara, R ;

Nakamura, Y ;

Kitagawa, H ;

Sugiura, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2507-2515

[9] Ti-catalyzed enantioselective addition of cyanide to imines.: A practical synthesis of optically pure α-amino acids [J].

Krueger, CA ;

Kuntz, KW ;

Dzierba, CD ;

Wirschun, WG ;

Gleason, JD ;

Snapper, ML ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4284-4285

[10] N-BOC-L-valine-connected amidomonophosphane rhodium(I) catalyst for asymmetric arylation of N-tosylarylimines with arylboroxines [J].

Kuriyama, M ;

Soeta, T ;

Hao, XY ;

Chen, O ;

Tomioka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8128-8129

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