Asymmetric copper-catalyzed synthesis of α-amino boronate esters from N-tert-butanesulfinyl aldimines

被引：190

作者：

Beenen, Melissa A. ^{[1
]}

An, Chihui ^{[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 | 2008年 / 130卷 / 22期

关键词：

D O I：

10.1021/ja800829y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and efficient new method for the asymmetric synthesis of a-amino boronate esters has been developed. The key step is the Cu(I)-catalyzed addition of bis(pinacolato)diboron to N-tert-butanesulfinyl aldimines, which proceeds in good yields (52-88%) and with very high diastereoselectivities (>96:2) for a variety of aldimine substrates. This method was applied to an efficient synthesis of bortezomib, a potent a-amino boronic acid inhibitor of the proteasome that is in clinical use for the treatment of multiple myeloma and mantle cell lymphoma.

引用

页码：6910 / +

页数：3

共 19 条

[1] 20S proteasome and its inhibitors: Crystallographic knowledge for drug development [J].

Borissenko, Ljudmila ;

Groll, Michael .

CHEMICAL REVIEWS, 2007, 107 (03) :687-717

[2] Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines [J].

Colyer, John T. ;

Andersen, Neil G. ;

Tedrow, Jason S. ;

Soukup, Troy S. ;

Faul, Margaret M. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) :6859-6862

[3] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[4] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

[5] TIN-COPPER TRANSMETALATION - CROSS-COUPLING OF ALPHA-HETEROATOM-SUBSTITUTED ALKYLTRIBUTYLSTANNANES WITH ORGANOHALIDES [J].

FALCK, JR ;

BHATT, RK ;

YE, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :5973-5982

[6] Direct synthesis of [alpha-[(tert-butoxycarbonyl)amino]alkyl]boronates from (alpha-haloalkyl)boronates [J].

Jadhav, PK ;

Man, HW .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7951-7954

[7]

KETTNER C, 1990, J BIOL CHEM, V265, P18289

[8] Catalytic diboration of aldehydes via insertion into the copper-boron bond [J].

Laitar, David S. ;

Tsui, Emily Y. ;

Sadighi, Joseph P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (34) :11036-11037

[9] Platinum catalyzed diboration using a commercially available catalyst:: Diboration of aldimines to α-aminoboronate esters [J].

Mann, G ;

John, KD ;

Baker, RT .

ORGANIC LETTERS, 2000, 2 (14) :2105-2108

[10]

Matteson DS, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P305, DOI 10.1002/3527606548.ch8

← 1 2 →