Stereoselective conjugate radical additions: Application of a fluorous oxazolidinone chiral auxiliary for efficient tin removal

被引：33

作者：

Hein, JE ^{[1
]}

Zimmerman, J ^{[1
]}

Sibi, MP ^{[1
]}

Hultin, PG ^{[1
]}

机构：

[1] Univ Manitoba, Dept Chem, Winnipeg, MB R3T 2N2, Canada

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol050956k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazoldinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.

引用

收藏

页码：2755 / 2758

页数：4

相关论文

共 38 条

[11] ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-HYDRAZONE RAMP-HYDRAZONE ENANTIOSELECTIVE SYNTHESIS OF PHEROMONES OF THE SMALL FOREST ANT (FORMICA-POLYCTENA) AND THE RED WOOD ANT (F-RUFA) [J].

ENDERS, D ;

RENDENBACH, BEM .

TETRAHEDRON, 1986, 42 (08) :2235-2242

[12] Free radical reactions on soluble supports from ring-opening metathesis [J].

Enholm, EJ ;

Gallagher, ME .

ORGANIC LETTERS, 2001, 3 (21) :3397-3399

[13]

GANESAN A, 2002, HDB COMBINATORIAL CH, V1, P227

[14] Hypophosphite mediated carbon-carbon bond formation: total synthesis of epialboatrin and structural revision of alboatrin [J].

Graham, SR ;

Murphy, JA ;

Kennedy, AR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (21) :3071-3073

[15] KF-silica as a stationary phase for the chromatographic removal of tin residues from organic compounds [J].

Harrowven, DC ;

Guy, IL .

CHEMICAL COMMUNICATIONS, 2004, (17) :1968-1969

[16]

Hein JE, 2003, SYNLETT, P635

[17] Diethylphosphine oxide (DEPO): High-yielding and facile preparation of indolones in water [J].

Khan, TA ;

Tripoli, R ;

Crawford, JJ ;

Martin, CG ;

Murphy, JA .

ORGANIC LETTERS, 2003, 5 (16) :2971-2974

[18] ASYMMETRIC-SYNTHESIS .6. COPPER SALT PROMOTED GRIGNARD-REAGENT ADDITIONS TO ETHYL 2,3-DIDEOXY-4,5-6,7-DI-O-ISOPROPYLIDENE-D-ARABINO-TRANS-HEPT-2-ENONATEAND SUBSEQUENT FORMATION OF OPTICALLY-ACTIVE 2-ALKYL (OR ARYL) BUTANE-1,4-DIOIC ACIDS AND BUTYRO-1,4-LACTONES [J].

LAWSTON, IW ;

INCH, TD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (11) :2629-2635

[19]

Leonard J, 1998, EUR J ORG CHEM, V1998, P2051

[20] Carbon-carbon bond construction on solid support: triethylborane-induced radical reactions of oxime ethers [J].

Miyabe, H ;

Nishimura, A ;

Fujishima, Y ;

Naito, T .

TETRAHEDRON, 2003, 59 (11) :1901-1907

← 1 2 3 4 →