A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines

被引：24

作者：

Dangerfield, Emma M. ^{[1
,2
]}

Gulab, Shivali A. ^{[3
]}

Plunkett, Catherine H. ^{[1
,2
]}

Timmer, Mattie S. M. ^{[1
]}

Stocker, Bridget L. ^{[2
]}

机构：

[1] Victoria Univ Wellington, Sch Chem & Phys Sci, Wellington, New Zealand

[2] Malaghan Inst Med Res, Wellington, New Zealand

[3] Ind Res Ltd, Lower Hutt, New Zealand

来源：

CARBOHYDRATE RESEARCH | 2010年 / 345卷 / 10期

关键词：

Pyrrolidine; Iminosugar; Carbamate; Reductive amination; Green chemistry; Protecting group free; MODELING CHEMICAL-REACTIVITY; REDUCTIVE AMINATION; PROTECTING-GROUP; GLYCOSIDASE INHIBITORS; ALPHA-GLUCOSIDASE; NATURAL OCCURRENCE; D-LYXOSE; DERIVATIVES; ALDEHYDES; KETONES;

D O I：

10.1016/j.carres.2010.03.016

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1360 / 1365

页数：6

共 58 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2] Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry [J].

Ali, Asghar ;

van den Berg, Richard J. B. H. N. ;

Overkleeft, Herman S. ;

Filippov, Dmitri V. ;

van der Marel, Gijsbert A. ;

Codee, Jeroen D. C. .

TETRAHEDRON LETTERS, 2009, 50 (19) :2185-2188

[3] Sugar-mimicking glycosidase inhibitors: bioactivity and application [J].

Asano, N. .

CELLULAR AND MOLECULAR LIFE SCIENCES, 2009, 66 (09) :1479-1492

[4] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].

Asano, N ;

Nash, RJ ;

Molyneux, RJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680

[5]

Baxter E.W., 2002, ORGANIC REACTIONS, V59, P1, DOI 10.1002/0471264180.or059.01

[6] ASYMMETRIC-SYNTHESIS OF 3S,4R-DIHYDROXYPYRROLIDINES BY REGIOSELECTIVE AND STEREOSELECTIVE HYDROXYLATION OF 4-OXOPROLINE ENOLATE [J].

BLANCO, MJ ;

SARDINA, FJ .

TETRAHEDRON LETTERS, 1994, 35 (45) :8493-8496

[7] C-3- and C-4-alkylated polyhydroxypyrrolidines: Enantiospecific syntheses and glycosidase inhibitory activity [J].

Blanco, MJ ;

Sardina, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3411-3416

[8] Activity and selectivity control in reductive amination of butyraldehyde over noble metal catalysts [J].

Bödis, J ;

Lefferts, L ;

Müller, TE ;

Pestman, R ;

Lercher, JA .

CATALYSIS LETTERS, 2005, 104 (1-2) :23-28

[9] POTENTIAL GLYCOSIDASE INHIBITORS - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO DERIVATIVES OF D-GLUCITOL, D-XYLITOL AND L-XYLITOL, D-ALLITOL AND L-ALLITOL, D-TALITOL AND L-TALITOL, AND D-GULITOL [J].

BUCHANAN, JG ;

LUMBARD, KW ;

STURGEON, RJ ;

THOMPSON, DK ;

WIGHTMAN, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :699-706

[10] GEOMETRICAL REACTION COORDINATES .2. NUCLEOPHILIC ADDITION TO A CARBONYL GROUP [J].

BURGI, HB ;

DUNITZ, JD ;

SHEFTER, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :5065-5067

← 1 2 3 4 5 6 →