Preparation of One-Carbon Homologated Amides from Aldehydes or Primary Alcohols

被引：36

作者：

Gupta, Manoj K. ^{[1
]}

Li, Zhexi ^{[1
]}

Snowden, Timothy S. ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 06期

基金：

美国国家科学基金会;

关键词：

METHOXY-N-METHYLAMIDES; ALPHA-HYDROXY ACIDS; CARBOXYLIC-ACIDS; ENANTIOSELECTIVE SYNTHESIS; TRICHLOROMETHYL KETONES; ARYL ALDEHYDES; CONVERSION; ESTERS;

D O I：

10.1021/ol500200n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldehydes and primary alcohols can be converted to one-carbon homologated primary, secondary, or tertiary amides in two operational steps. The approach offers several unique features including compatibility with (hetero)-aryl, alkyl, alkenyl, and racemizable chiral substrates, the ability to prepare Weinreb amides from aryl and unhindered aliphatic substrates, and the opportunity to employ unprotected amino acids as amine sources in the amidation step.

引用

下载

页码：1602 / 1605

页数：4

共 50 条

[1] Efficient transformations of aldehydes and ketones into one-carbon homologated carboxylic acids
Katritzky, AR
Toader, D
Xie, LH
SYNTHESIS-STUTTGART, 1996, (12): : 1425 - &
[2] A facile one-carbon homologation of aryl aldehydes to amides
Shen, W
Kunzer, A
ORGANIC LETTERS, 2002, 4 (08) : 1315 - 1317
[3] A new method for the synthesis of α-thio aldehydes and alcohols from aldehydes with one-carbon elongation
Satoh, T
Kubota, K
TETRAHEDRON LETTERS, 2000, 41 (13) : 2121 - 2124
[4] NOVEL CONVERSION OF EPOXIDES TO ONE-CARBON HOMOLOGATED ALLYLIC ALCOHOLS BY DIMETHYLSULFONIUM METHYLIDE
ALCARAZ, L
HARNETT, JJ
MIOSKOWSKI, C
MARTEL, JP
LEGALL, T
SHIN, DS
FALCK, JR
TETRAHEDRON LETTERS, 1994, 35 (30) : 5449 - 5452
[5] A novel conversion of erythro phospholane epoxides to one-carbon atom homologated allylic alcohols
Reddy, VK
Haritha, B
Oshikawa, T
Yamashita, M
TETRAHEDRON LETTERS, 2004, 45 (13) : 2851 - 2854
[6] One-Carbon Homologation of Primary Alcohols and the Reductive Homologation of Aldehydes Involving a Jocic-Type Reaction
Li, Zhexi
Gupta, Manoj K.
Snowden, Timothy S.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (32) : 7009 - 7019
[7] ONE-CARBON HOMOLOGATION OF ALDEHYDES AND KETONES TO CARBOXYLIC-ACIDS, ESTERS AND AMIDES
WATT, DS
DINIZO, SE
FREERKSEN, RW
PABST, WE
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1976, 172 (SEP3): : 42 - 42
[8] STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .1. SYNTHESIS OF ONE-CARBON HOMOLOGOUS ALLYL ALCOHOLS FROM ALDEHYDES OR KETONES
HOFFMANN, RW
GOLDMANN, S
MAAK, N
GERLACH, R
FRICKEL, F
STEINBACH, G
CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (03): : 819 - 830
[9] One-Carbon Homologation of Primary Alcohols to Carboxylic Acids, Esters, and Amides via Mitsunobu Reactions with MAC Reagents
Kagawa, Natsuko
Nibbs, Antoinette E.
Rawal, Viresh H.
ORGANIC LETTERS, 2016, 18 (10) : 2363 - 2366
[10] A novel preparation of methyl ketones through one-carbon homologation of aldehydes
Wang, L
Li, PH
Yan, JC
Wu, ZZ
TETRAHEDRON LETTERS, 2003, 44 (25) : 4685 - 4688

← 1 2 3 4 5 →