Platinum-Catalyzed Isomerization of Cyclopropenes to 1,3-Dienes

被引：0

作者：

Smyrnov, Vladyslav ^{[1
]}

Homassel, Antonin ^{[1
]}

Choudhury, Leander ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Catalysis & Organ Synth, EPFL,SB,ISIC,LCSO, BCH 4306, CH-1015 Lausanne, Switzerland

来源：

HELVETICA CHIMICA ACTA | 2024年 / 107卷 / 09期

基金：

瑞士国家科学基金会;

关键词：

cyclopropene; isomerization; catalysis; diene; platinum; DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; REGIOSELECTIVE BUTA-1,3-DIENYLATION; ASYMMETRIC-SYNTHESIS; ALDEHYDES; HOMOALLENYLBORATION; CYCLOISOMERIZATION; ACID; DERIVATIVES; DISCOVERY;

D O I：

10.1002/hlca.202400105

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we report a platinum-catalyzed isomerization of cyclopropenes to 1,3-dienes. Diverse dienylated alcohols were obtained in 42-98 % yield. The synthetic potential of the products was demonstrated by their use in Diels-Alder cycloadditions with various dienophiles. Isotope labelling studies provide strong support for a mechanism involving pericyclic [1,5]-sigma-bond rearrangement of a vinyl platinum carbene intermediate. image

引用

页数：7

共 64 条

[1] Metal-mediated carbonyl-1,3-butadien-2-ylation by 1,4-bis(methanesulfonyl)-2-butyne or 1,4-dibromo-2-butyne in aqueous media:: Asymmetric synthesis of 3-substituted 3-hydroxy-β-lactams [J].

Alcaide, B ;

Almendros, P ;

Rodríguez-Acebes, R .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1925-1928

[2] Novel enantioselective synthesis of 1,3-butadien-2-ylmethanols via tandem alkylbromide-epoxide vinylations using dimethylsulfonium methylide [J].

Alcaraz, L ;

Cox, K ;

Cridland, AP ;

Kinchin, E ;

Morris, J ;

Thompson, SP .

ORGANIC LETTERS, 2005, 7 (07) :1399-1401

[3] Highly Efficient Stereoselective Catalytic C(sp3)?H Insertions with Donor Rhodium Carbenoids Generated from Cyclopropenes [J].

Archambeau, Alexis ;

Miege, Frederic ;

Meyer, Christophe ;

Cossy, Janine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (46) :11540-11544

[4] THE PREPARATION AND LITHIATION OF 1-HALOGENOCYCLOPROPENES [J].

BAIRD, MS ;

HUSSAIN, HH ;

NETHERCOTT, W .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (10) :1845-1853

[5] Regioselective Carbon-Carbon Bond Cleavage in the Oxidation of Cyclopropenylcarbinols [J].

Basheer, Ahmad ;

Mishima, Masaaki ;

Marek, Ilan .

ORGANIC LETTERS, 2011, 13 (15) :4076-4079

[6] Construction of [4-3.1]propellanes via molybdenum Fischer carbene complexes [J].

Bertolini, TM ;

Nguyen, QH ;

Harvey, DF .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8675-8678

[7] CODIMERIZATION OF 3,3-DIMETHYLCYCLOPROPENE WITH ETHYLENECARBOXYLIC ESTERS AT NICKEL(O) CATALYSTS [J].

BINGER, P ;

MCMEEKIN.J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1974, 13 (07) :466-467

[8] THERMAL AND CATALYZED DIELS-ALDER REACTIONS WITH CHIRAL 2-SUBSTITUTED-1,3-DIENES - CONFORMATIONAL MODELS FOR DIASTEREOFACIAL SELECTIVITY [J].

BLOCH, R ;

CHAPTALGRADOZ, N .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4162-4169

[9] Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C-H Functionalizations [J].

Burns, David J. ;

Lam, Hon Wai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) :9931-9935

[10] On the mechanism of homogeneous Pt-catalysis: A theoretical view [J].

Chen, Haohua ;

Li, Yuanyuan ;

Liu, Song ;

Xiong, Qin ;

Bai, Ruopeng ;

Wei, Donghui ;

Lan, Yu .

COORDINATION CHEMISTRY REVIEWS, 2021, 437

← 1 2 3 4 5 6 7 →