The enantiospecific synthesis of chromanes and isochromanes using a variant of an intramolecular Nicholas reaction

被引：13

作者：

Tyrrell, Elizabeth ^{[1
]}

Mazloumi, Khatebeh ^{[1
]}

Banti, Donatella ^{[1
]}

Sajdak, Paulina ^{[1
]}

Sinclair, Alex ^{[1
]}

Le Gresley, Adam ^{[1
]}

机构：

[1] Kingston Univ, Sch Chem & Pharm, Kingston KT1 2EE, Surrey, England

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 33期

关键词：

Nicholas cyclisation; Chromane; Isochromane; Asymmetric alkynylation; N-Methylephedrine; Enantiospecific reaction; ENANTIOSELECTIVE ALKYNYLATION REACTIONS; IN-SITU GENERATION; ALDEHYDES; BENZOPYRANS; SUBSTITUENTS; CHEMISTRY; ALCOHOLS; FACILE; MILD;

D O I：

10.1016/j.tetlet.2012.05.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiospecific synthesis of chromanes and isochromanes obtained from an intramolecular Nicholas cyclisation reaction is discussed. During the course of this study we observed the formation of chroman-4-ones from a CAN deprotection step of a dioxolane and this is also discussed. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4280 / 4282

页数：3

共 50 条

[1] THE ENANTIOSPECIFIC NICHOLAS REACTION
MUEHLDORF, AV
GUZMANPEREZ, A
KLUGE, AF
TETRAHEDRON LETTERS, 1994, 35 (47) : 8755 - 8758
[2] Intramolecular Heck reaction for the synthesis of isochromanes under ambient and high pressure
Tietze, LF
Burkhardt, O
Henrich, M
LIEBIGS ANNALEN-RECUEIL, 1997, (05): : 887 - 891
[3] Synthesis of Tenuifolin through Intramolecular Nicholas Reaction
Djurdjevic, Sinisa
Green, James R.
SYNLETT, 2014, 25 (17) : 2467 - 2470
[4] A diastereoselective synthesis of benzopyrans using a novel intramolecular Nicholas reaction.
Muller, C
Tyrrell, E
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 588 - ORGN
[5] Synthesis of benzoxocine heliannuols via the intramolecular Nicholas reaction
St Onge, Brent
Green, James
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
[6] Stereoselective intramolecular Nicholas reaction using epoxides as nucleophiles
Crisóstomo, FRP
Martín, T
Martín, VS
ORGANIC LETTERS, 2004, 6 (04) : 565 - 568
[7] The synthesis of bridged and fused ring carbocycles using a novel variation of an intramolecular Nicholas reaction
Tyrrell, E
Skinner, GA
Bashir, T
SYNLETT, 2001, (12) : 1929 - 1931
[8] A diastereoselective synthesis of benzopyrans using a novel intramolecular Nicholas reaction in the key cyclisation step
Berge, J
Claridge, S
Mann, A
Muller, C
Tyrrell, E
TETRAHEDRON LETTERS, 1997, 38 (04) : 685 - 686
[9] Intramolecular Nicholas Reaction Enables the Stereoselective Synthesis of Strained Cyclooctynes
Monzon, Diego M.
Manuel Betancort, Juan
Martin, Tomas
Angel Ramirez, Miguel
Martin, Victor S.
Diaz Diaz, David
MOLECULES, 2021, 26 (06):
[10] Gold catalysis:: Dihydroisobenzofurans and isochromanes by the intramolecular furan/alkyne reaction
Hashmi, A. Stephen K.
Woelfle, M.
Ata, Filiz
Hamzic, Melissa
Salathe, Ralph
Frey, Wolfgang
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) : 2501 - 2508

← 1 2 3 4 5 →