Remarkably stable tetrahedral intermediates:: Carbinols from nucleophilic additions to N-acylpyrroles

被引：0

作者：

Evans, DA ^{[1
]}

Borg, G ^{[1
]}

Scheidt, KA ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2002年 / 41卷 / 17期

关键词：

D O I：

10.1002/1521-3773(20020902)41:17<3188::AID-ANIE3188>3.0.CO;2-H

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sufficiently stable intermediates formed in the reaction of N-acylpyrroles (1) with hydride and Grignard reagents can undergo further synthetic transformations and chromatographic purification to enable the generation of pyrrolecarbinols 2 in 76-95% yields [Eq. (1)].

引用

页码：3188 / +

页数：5

共 27 条

[1] Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles
Castoldi, Laura
Holzer, Wolfgang
Langer, Thierry
Pace, Vittorio
CHEMICAL COMMUNICATIONS, 2017, 53 (68) : 9498 - 9501
[2] A new method to N-arylmethylenepyrroles from N-acylpyrroles
DSilva, C
Iqbal, R
SYNTHESIS-STUTTGART, 1996, (04): : 457 - &
[3] Proximity Effects in Nucleophilic Addition Reactions to Medium-Bridged Twisted Lactams: Remarkably Stable Tetrahedral Intermediates
Szostak, Michal
Yao, Lei
Aube, Jeffrey
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) : 2078 - 2084
[4] A convenient synthesis of N-acylpyrroles from primary aromatic amides
Ekkati, AR
Bates, DK
SYNTHESIS-STUTTGART, 2003, (13): : 1959 - 1961
[5] Facile and convenient synthesis of N-acylpyrroles from primary aromatic amides
Ekkati, AR
Bates, DK
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U384 - U384
[6] BASE-CATALYZED HYDROLYSIS OF N-ACYLPYRROLES - MEASURABLE ACIDITY OF A STEADY-STATE TETRAHEDRAL INTERMEDIATE
MENGER, FM
DONOHUE, JA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 432 - 437
[7] Highly Enantioselective Conjugate Additions of Phosphites to α,β-Unsaturated N-Acylpyrroles and Imines: A Practical Approach to Enantiomerically Enriched Amino Phosphonates
Zhao, Depeng
Wang, Yuan
Mao, Lijuan
Wang, Rui
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (41) : 10983 - 10987
[8] Highly Regio-, Diastereo-, and Enantioselective 1,6-and 1,8-Additions of Azlactones to Di- and Trienyl N-Acylpyrroles
Uraguchi, Daisuke
Yoshioka, Ken
Ueki, Yusuke
Ooi, Takashi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (47) : 19370 - 19373
[9] A Practical Preparation of Highly Versatile N-Acylpyrroles from 2,4,4-Trimethoxybutan-1-amine
Maehara, Tomoaki
Kanno, Rentaro
Yokoshima, Satoshi
Fukuyama, Tohru
ORGANIC LETTERS, 2012, 14 (07) : 1946 - 1948
[10] Nucleophilic Capture of the Imino-Quinone Methide Type Intermediates Generated from 2-Aminothiazol-5-yl Carbinols
Saulnier, Mark G.
Dodier, Marco
Frennesson, David B.
Langley, David R.
Vyas, Dolatrai M.
ORGANIC LETTERS, 2009, 11 (22) : 5154 - 5157

← 1 2 3 →