Highly Stereoselective Synthesis of Terminal Chloro-Substituted Propargylamines and Further Functionalization

被引：9

作者：

Jordan, Savannah ^{[1
]}

Starks, Samuel A. ^{[1
]}

Whatley, Michael F. ^{[1
]}

Turlington, Mark ^{[1
]}

机构：

[1] Berry Coll, Dept Chem, Mt Berry, GA 30149 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 19期

关键词：

ENANTIOSELECTIVE 3-COMPONENT SYNTHESIS; PROMOTED DIASTEREOSELECTIVE SYNTHESIS; ZINC/BINOL-CATALYZED ALKYNYLATION; OPTICALLY-ACTIVE PROPARGYLAMINES; CHIRAL PROPARGYLAMINES; ASYMMETRIC-SYNTHESIS; AMINES; CYCLOISOMERIZATION; ALDIMINES; ALDEHYDES;

D O I：

10.1021/acs.orglett.5b02408

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly stereoselective addition of lithiated chloroacetylene, derived in situ from cis-1,2-dichloroethene and methyl lithium, to Ellman chiral N-tert-butanesulfinyl imines is reported. The reaction proceeds in high yield (up to 98%) and with excellent diastereoselectivity (up to >20:1) for a variety of aryl, heteroaromatic, alkyl, and alpha,beta-unsaturated imine substrates. Transformations of the terminal chloro-substituted propargylamine products are described in which lithium-halogen exchange yields nucleophilic acetylides that can be quenched to yield terminal alkynes or intercepted by carbon electrophiles.

引用

页码：4842 / 4845

页数：4

共 50 条

[41] PEPTIDOMIMETIC SYNTHESIS - A NOVEL, HIGHLY STEREOSELECTIVE ROUTE TO SUBSTITUTED FREIDINGER LACTAMS
ROBL, JA
CIMARUSTI, MP
SIMPKINS, LM
WELLER, HN
PAN, YY
MALLEY, M
DIMARCO, JD
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2348 - 2355
[42] HIGHLY STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED HYDRINDANES RELATED TO THE ANTIEPILEPTIC DRUG TOPIRAMATE
GRECO, MN
MARYANOFF, BE
TETRAHEDRON LETTERS, 1992, 33 (35) : 5009 - 5012
[43] Highly stereoselective N-terminal functionalization of small peptides by chiral phase-transfer catalysis
Ooi, T
Tayama, E
Maruoka, K
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (05) : 579 - +
[44] HIGHLY STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED HYDRINDANES RELATED TO THE ANTIEPILEPTIC DRUG TOPIRAMATE
GRECO, MN
MARYANOFF, BE
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 84 - ORGN
[45] Synthesis and functionalization of highly substituted oxetanes: Molecular scaffolds for drug discovery
Davis, Owen
Bull, James
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
[46] Highly regioselective and stereoselective radical addition of p-TsBr to substituted terminal allenes and their nucleophilic substitutions: Synthesis of α,β-unsaturated sulfones
Kang, S.-K.
Seo, H.-W.
Ha, Y.-H.
2001, Georg Thieme Verlag
[47] Highly regioselective and stereoselective radical addition of p-TsBr to substituted terminal allenes and their nucleophilic substitutions:: Synthesis of α,β-unsaturated sulfones
Kang, SK
Seo, HW
Ha, YH
SYNTHESIS-STUTTGART, 2001, (09): : 1321 - 1326
[48] Highly efficient one-pot synthesis of D-ring chloro-substituted neocryptolepines via a condensation-Pd-catalyzed intramolecular direct arylation strategy
Hostyn, Steven
Tehrani, Kourosch Abbaspour
Lemiere, Filip
Smout, Veerle
Maes, Bert U. W.
TETRAHEDRON, 2011, 67 (03) : 655 - 659
[49] Synthesis, antioxidant, in silico and computational investigation of 2,5-dihydroxyacetophenone derived chloro-substituted hydroxychalcones, hydroxyflavanones and hydroxyflavindogenides
Siddiqa, Aysha
Tajammal, Affifa
Irfan, Ahmad
Munawar, Munawar Ali
Azam, Muhammad
Basra, Muhammad Asim Raza
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 2021,
[50] Aryloxy- and chloro-substituted zinc(II) phthalocyanine dyes: Synthesis, characterization, and application for reducing the thickness of color filters
Namgoong, Jin Woong
Kim, Se Hun
Chung, Sei-Won
Kim, Young Hoon
Kwak, Moo Sun
Kim, Jae Pil
DYES AND PIGMENTS, 2018, 154 : 128 - 136

← 1 2 3 4 5 →