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.

引用

页码：3977 / 3980

页数：4

共 49 条

[1] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy
Bharadwaj, AR
Scheidt, KA
[J]. ORGANIC LETTERS, 2004, 6 (14) : 2465 - 2468
[2] Synthesis and use of α-silyl-substituted α-hydroxyacetic acids
Bolm, C
Kasyan, A
Heider, P
Saladin, S
Drauz, K
Günther, K
Wagner, C
[J]. ORGANIC LETTERS, 2002, 4 (13) : 2265 - 2267
[3] BONINI BF, 1995, SYNTHESIS-STUTTGART, P92
[4] SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS
BROOK, AG
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (03) : 77 - 84
[5] SYNTHESIS OF SILYL AND GERMYL KETONES
BROOK, AG
DUFF, JM
NONES, PF
DAVIS, NR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) : 431 - &
[6] MECHANISM OF ALPHA-SILYLCARBINOL TO SILYL ETHER REARRANGEMENT
BROOK, AG
LEGROW, GE
MACRAE, DM
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1967, 45 (03): : 239 - &
[7] The reaction of phenyldimethylsilyllithium with N-phenylpyrrolidone
Buswell, M
Fleming, I
[J]. CHEMICAL COMMUNICATIONS, 2003, (02) : 202 - 203
[8] ASYMMETRIC ALLYLBORATION OF ACYLSILANES
BUYNAK, JD
GENG, BL
UANG, SN
STRICKLAND, JB
[J]. TETRAHEDRON LETTERS, 1994, 35 (07) : 985 - 988
[9] EASY ONE-STEP GENERAL-SYNTHESIS OF ACYLSILANES
CAPPERUCCI, A
DEGL'INNOCENTI, A
FAGGI, C
RICCI, A
DEMBECH, P
SECONI, G
[J]. 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
Chuang, TH
Fang, JM
Jiaang, WT
Tsai, YM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) : 1794 - 1805

← 1 2 3 4 5 →