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

页码：1602 / 1605

页数：4

共 50 条

[21] One-carbon homologation of aldehydes to N-(α-haloacyl)benzotriazoles
Katritzky, Alan R.
Tala, Srinivasa R.
Singh, Sandeep K.
SYNTHESIS-STUTTGART, 2006, (19): : 3231 - 3237
[22] ORGANOBORANES .42. ONE-CARBON HOMOLOGATION OF ORGANOBORANES - SYNTHESIS OF HOMOLOGATED BORONIC ACIDS AND ESTERS FROM BORONIC ESTERS
BROWN, HC
NAIK, RG
SINGARAM, B
PYUN, C
ORGANOMETALLICS, 1985, 4 (11) : 1925 - 1929
[23] PREPARATION OF CARBOXYLIC AMIDES FROM ALDEHYDES BY OXIDATION
GILMAN, NW
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (14): : 733 - &
[24] FORMAMIDINE ANIONS IN SYNTHESIS - THE ONE-CARBON HOMOLOGATION OF ALDEHYDES AND KETONES TO NITRILES
SANTIAGO, B
MEYERS, AI
TETRAHEDRON LETTERS, 1993, 34 (37) : 5839 - 5842
[25] A NEW METHOD FOR THE SYNTHESIS OF ACYLSILANES VIA ONE-CARBON HOMOLOGATION OF ALDEHYDES
YOSHIDA, J
MATSUNAGA, S
ISHICHI, Y
MAEKAWA, T
ISOE, S
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03): : 1307 - 1309
[26] PHOSPHONATE REAGENTS FOR THE SYNTHESIS OF ENOL ETHERS AND ONE-CARBON HOMOLOGATION TO ALDEHYDES
KLUGE, AF
CLOUDSDALE, IS
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (26): : 4847 - 4852
[27] Recent approaches towards one-carbon homologation-functionalization of aldehydes
Sebastian, Sharol
Monika
Khatana, Anil Kumar
Yadav, Eqvinshi
Gupta, Manoj K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (14) : 3055 - 3074
[28] MIGRATORY INSERTION REACTIONS OF ORGANOMETALLICS .2. ONE-POT CONVERSION OF ALKYNES AND ALKENES INTO ONE-CARBON HOMOLOGATED ALDEHYDES VIA HYDROZIRCONATION-ISOCYANIDE INSERTION-HYDROLYSIS
NEGISHI, E
SWANSON, DR
MILLER, SR
TETRAHEDRON LETTERS, 1988, 29 (14) : 1631 - 1634
[29] New one-carbon degradative transformation of β-alkyl-β-azido alcohols
Fan, QH
Ni, NT
Li, Q
Zhang, LH
Ye, XS
ORGANIC LETTERS, 2006, 8 (05) : 1007 - 1009
[30] OXIDATION WITH NICKEL PEROXIDE . A NEW SYNTHESIS OF AMIDES FROM ALDEHYDES OR ALCOHOLS
NAKAGAWA, K
ONOUE, H
MINAMI, K
CHEMICAL COMMUNICATIONS, 1966, (01) : 17 - &

← 1 2 3 4 5 →