Hetero-Diels-Alder Addition of Ethyl 2-Nitrosoacrylate to ( Z )-Prop-1-enyl Ethers. Stereoselective Synthesis of a Precursor to Sacubitril

被引：2

作者：

Zisopoulou, Stavroula A. ^{[1
]}

Andreou, Thanos ^{[2
]}

Koftis, Theocharis V. ^{[2
]}

Gallos, John K. ^{[1
]}

Stathakis, Christos I. ^{[1
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Thessaloniki 54124, Greece

[2] Pharmathen Ind SA, 9th Km Thermi Thessaloniki, Thessaloniki 57001, Greece

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 10期

关键词：

sacubitril; hetero-Diels-Alder reaction; nitrosoalkenes; oxazinanes; chiral auxiliary; HEART-FAILURE; ASYMMETRIC-SYNTHESIS; NITROSOALKENE; ISOMERIZATION; NEPRILYSIN; CATALYSTS; ALKENES; CONCISE; ROUTE;

D O I：

10.1055/a-2029-0015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, conceptually distinct synthesis of a key precursor to sacubitril, an antihypertensive drug, is presented. The well -demonstrated hetero-Diels-Alder addition of in situ generated nitrosoalkenes to electron-rich enol ethers was engaged to establish the required functionalities with controllable relative stereochemistry. An asymmetric variant of the enol ether enabled access to the target molecule in enantiopure form.

引用

页码：1507 / 1516

页数：10

共 13 条

[1] Synthesis of C-glycosylated amino acids by hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to exo-glycals
Massen, Zoe S.
Sarli, Vassiliki C.
Coutouli-Argyropoulou, Evdoxia
Gallos, John K.
CARBOHYDRATE RESEARCH, 2011, 346 (02) : 230 - 237
[2] Hetero-Diels-Alder reaction of ethyl 2-nitrosoacrylate and cyclohexadienes, and bromine induced diene isomerization
Song, Jian
Lin, Yongcheng
Szeto, Yau Shan
Chan, Wing Lai
HETEROCYCLES, 2006, 68 (08) : 1685 - 1689
[3] The hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to electron-rich alkenes as a route to unnatural α-amino acids
Gallos, JK
Sarli, VC
Varvogli, AC
Papadoyanni, CZ
Papaspyrou, SD
Argyropoulos, NG
TETRAHEDRON LETTERS, 2003, 44 (20) : 3905 - 3909
[4] Asymmetric Synthesis of Both Enantiomers of Protected 5-Hydroxynorvaline by Hetero-Diels-Alder Addition of ethyl 2-Nitrosoacrylate to (R)- and (S)-1-Phenylbutyl Vinyl Ether
Massen, Zoe S.
Gallos, John K.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (05) : 1214 - 1217
[5] Synthesis of a protected trihydroxyindolizidine 3-carboxylate via a hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to a D-ribose-derived exo-glycal
Massen, Zoe S.
Coutouli-Argyropoulou, Evdoxia
Sarli, Vassiliki C.
Gallos, John K.
CARBOHYDRATE RESEARCH, 2011, 346 (04) : 508 - 511
[6] Stereoselective hetero-Diels-Alder reaction of 3-(polyfluoroacyl)chromones with enol ethers. Novel synthesis of 2-RF-containing nicotinic acid derivatives
Sosnovskikh, Vyacheslav Ya.
Khalymbadzha, Igor A.
Irgashev, Roman A.
Slepukhin, Pavel A.
TETRAHEDRON, 2008, 64 (44) : 10172 - 10180
[7] 1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in synthesis: Stereoselective homo- and hetero-Diels-Alder reactions
Adelbrecht, JC
Craig, D
Fleming, AJ
Martin, FM
SYNLETT, 2005, (17) : 2643 - 2647
[8] Stereoselective hetero-Diels-Alder reaction of 3-(trifluoroacetyl)chromones with cyclic enol ethers:: synthesis of 3-aroyl-2-(trifluoromethyl)pyridines with ω-hydroxyalkyl groups
Sosnovskikh, Vyacheslav Ya.
Irgashev, Roman A.
Khalymbadzha, Igor A.
Slepukhin, Pavel A.
TETRAHEDRON LETTERS, 2007, 48 (36) : 6297 - 6300
[9] Hetero-Diels-Alder reaction of 3-aryl-2-benzoyl-2-propenenitriles with enol ethers. Synthesis of 2-alkoxy-3,4-dihydro-2H-pyran-5-carbonitriles
BogdanowiczSzwed, K
Palasz, A
MONATSHEFTE FUR CHEMIE, 1997, 128 (11): : 1157 - 1172
[10] Synthesis of 2-(arylsulfonyl)-4-hydroxypyridines by hetero-Diels-Alder reaction of 1,3-bis-silyl enol ethers with arylsulfonyl cyanides
Emmrich, Thomas
Reinke, Helmut
Langer, Peter
SYNTHESIS-STUTTGART, 2006, (15): : 2551 - 2555

← 1 2 →