Efficient synthesis of acylsilanes using morpholine amides

被引：38

作者：

Clark, CT ^{[1
]}

Milgram, BC ^{[1
]}

Scheidt, KA ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 22期

关键词：

D O I：

10.1021/ol0483854

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A general synthesis of acylsilanes from the corresponding morpholine amides and silyllithium species is described. The use of morpholine amides is economical and prevents over-addition by the silyl nucleophile. The procedure cleanly affords acylsilanes in good yields and circumvents the use of stoichiometric copper(I) cyanide typically employed to synthesize these compounds from acid chlorides.

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页码：3977 / 3980

页数：4

相关论文

共 49 条

[1] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy [J].

Bharadwaj, AR ;

Scheidt, KA .

ORGANIC LETTERS, 2004, 6 (14) :2465-2468

[2] Synthesis and use of α-silyl-substituted α-hydroxyacetic acids [J].

Bolm, C ;

Kasyan, A ;

Heider, P ;

Saladin, S ;

Drauz, K ;

Günther, K ;

Wagner, C .

ORGANIC LETTERS, 2002, 4 (13) :2265-2267

[3]

BONINI BF, 1995, SYNTHESIS-STUTTGART, P92

[4] SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS [J].

BROOK, AG .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (03) :77-84

[5] SYNTHESIS OF SILYL AND GERMYL KETONES [J].

BROOK, AG ;

DUFF, JM ;

NONES, PF ;

DAVIS, NR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) :431-&

[6] MECHANISM OF ALPHA-SILYLCARBINOL TO SILYL ETHER REARRANGEMENT [J].

BROOK, AG ;

LEGROW, GE ;

MACRAE, DM .

CANADIAN JOURNAL OF CHEMISTRY, 1967, 45 (03) :239-&

[7] The reaction of phenyldimethylsilyllithium with N-phenylpyrrolidone [J].

Buswell, M ;

Fleming, I .

CHEMICAL COMMUNICATIONS, 2003, (02) :202-203

[8] ASYMMETRIC ALLYLBORATION OF ACYLSILANES [J].

BUYNAK, JD ;

GENG, BL ;

UANG, SN ;

STRICKLAND, JB .

TETRAHEDRON LETTERS, 1994, 35 (07) :985-988

[9] EASY ONE-STEP GENERAL-SYNTHESIS OF ACYLSILANES [J].

CAPPERUCCI, A ;

DEGL'INNOCENTI, A ;

FAGGI, C ;

RICCI, A ;

DEMBECH, P ;

SECONI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3612-3614

[10] Reductions, reductive alkylations, and intramolecular cyclizations of acyl silanes with samarium diiodide or tributyltin hydride [J].

Chuang, TH ;

Fang, JM ;

Jiaang, WT ;

Tsai, YM .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1794-1805

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