87184-80-3 (5-(叔丁基二甲基硅氧基)戊醛,5-((tert-Butyldimethylsilyl)oxy)pentanal)

_100%

反应条件：

1.1 Catalysts: 2,2′-Bipyridine , 1-Methylimidazole , Tempo , Tetrakis(acetonitrile)copper(1+) tetrafluoroborate Solvents: Acetonitrile ; rt

参考文献：

Gold-Catalyzed Asymmetric Transformation of Hydroxylated Propargylic Esters

Quintanilla, Carlos D. ; et al, ChemPlusChem, 2023, 88(10),

合成路线：1 步

_100%

反应条件：

1.1 Reagents: Tempo , Iodobenzene diacetate Solvents: Dichloromethane ; 5 h, rt
1.2 Reagents: Sodium thiosulfate Solvents: Water

参考文献：

Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis

Uchida, Miho; et al, Journal of Antibiotics, 2011, 64(12), 781-787

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Sodium bicarbonate , Sodium hypochlorite , Potassium bromide Catalysts: Tempo Solvents: Dichloromethane , Water ; 0 °C; 15 min, 0 °C
1.2 Reagents: Sodium thiosulfate Solvents: Water ; 5 min, 0 °C

参考文献：

Vicinal Bisheterocyclizations of Alkynes via Nucleophilic Interception of a Catalytic Platinum Carbene

Allegretti, Paul A.; et al, Journal of the American Chemical Society, 2013, 135(46), 17266-17269

合成路线：1 步

1401911-67-8

_97%

反应条件：

1.1 Reagents: Triphenylphosphine

参考文献：

1,5-Stereocontrol Using Silicon-containing Compounds

Maiti, Pranab, 2002, , ,

合成路线：1 步

61362-77-4

_94%

反应条件：

1.1 Reagents: Isopropylamine Catalysts: (OC-6-33)-Bis[N-[2,6-bis(1-methylethyl)phenyl]benzamidato-κN,κO]bis(N-ethylethan… Solvents: Benzene ; 24 h, 65 °C
1.2 Reagents: Silica

参考文献：

An easy-to-use, regioselective, and robust bis(amidate) titanium hydroamination precatalyst: mechanistic and synthetic investigations toward the preparation of tetrahydroisoquinolines and benzoquinolizine alkaloids

Zhang, Zhe; et al, Chemistry - A European Journal, 2007, 13(7), 2012-2022

合成路线：1 步

61362-77-4

_94%

反应条件：

1.1 Reagents: Isopropylamine Catalysts: (OC-6-33)-Bis[N-[2,6-bis(1-methylethyl)phenyl]benzamidato-κN,κO]bis(N-ethylethan… Solvents: Benzene ; 24 h, 65 °C; 65 °C → rt
1.2 Reagents: Silica Solvents: Dichloromethane ; 10 h, rt

参考文献：

Anti-Markovnikov Intermolecular Hydroamination: A Bis(amidate) Titanium Precatalyst for the Preparation of Reactive Aldimines

Zhang, Zhe; et al, Organic Letters, 2003, 5(24), 4733-4736

合成路线：1 步

796842-74-5

_91%

反应条件：

1.1 Reagents: Sodium bicarbonate , Ozone Solvents: Methanol , Dichloromethane ; rt → -78 °C; 3.5 h, -78 °C
1.2 Reagents: Dimethyl sulfide ; -78 °C → rt

参考文献：

Syntheses of stereochemically diverse nine-membered ring-containing biaryls

Krishnan, Shyam; et al, Organic Letters, 2004, 6(22), 4021-4024

合成路线：1 步

85807-84-7

_82%

反应条件：

1.1 Reagents: Triphenylphosphine , Ozone Solvents: Dichloromethane ; -78 °C; -78 °C → rt

参考文献：

Perhydrolysis in Ethereal H2O2 Mediated by MoO2(acac)2: Distinct Chemoselectivity between Ketones, Ketals, and Epoxides

An, Xiaosheng; et al, Organic Letters, 2019, 21(5), 1542-1546

合成路线：1 步

85807-84-7

参考文献：

A New Henry/Michael/Retro-Henry/Henry Domino Sequence Promoted by Bifunctional Organocatalysts

Quintavalla, Arianna; et al, Advanced Synthesis & Catalysis, 2013, 355(5), 938-946

合成路线：2 步

85807-84-7

反应条件：

1.1 Reagents: Dimethyl sulfide , Sodium bicarbonate , Ozone Solvents: Methanol , Dichloromethane
2.1 Reagents: Dimethyl sulfide Solvents: Dichloromethane

参考文献：

1,5-Stereocontrol Using Silicon-containing Compounds

Maiti, Pranab, 2002, , ,

合成路线：1 步

_75%

反应条件：

1.1 Reagents: Imidazole
1.2 Reagents: Dimethyl sulfoxide , Oxalyl chloride , Triethylamine

参考文献：

Highly Stereoselective Total Synthesis of Fully Hydroxy-Protected Mycolactones A and B and Their Stereoisomerization upon Deprotection

Wang, Guangwei; et al, Chemistry - A European Journal, 2011, 17(15), 4118-4130

合成路线：1 步

_70%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; 30 min, -78 °C
1.2 Solvents: Tetrahydrofuran ; 10 min, -78 °C; -78 °C → 23 °C; 3 h, 23 °C
1.3 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; -78 °C; 10 min, -78 °C
1.4 -78 °C; 15 min, -78 °C
1.5 Reagents: Triethylamine ; 15 min, -78 °C; -78 °C → 23 °C; 1 h, 23 °C
1.6 Reagents: Water ; 23 °C

参考文献：

Generation of α,β-unsaturated platinum carbenes from homopropargylic alcohols: rearrangements to polysubstituted furans

Allegretti, Paul A.; et al, Organic Letters, 2011, 13(21), 5924-5927

合成路线：1 步

_49%

反应条件：

1.1 Reagents: Triethylamine Solvents: Dichloromethane ; 2 h, 0 °C
1.2 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 1 h, rt

参考文献：

Palladium-catalyzed allylic alkylation of optically active α-alkenyl-α-acyloxytrialkylsilane

Sakaguchi, Kazuhiko; et al, Tetrahedron Letters, 2005, 46(30), 5009-5012

合成路线：1 步

参考文献：

Studies towards the Total Synthesis of Kadcotrione B

Reddy, Julakanti Satyanarayana; et al, Synthesis, 2020, 52(5), 735-743

合成路线：2 步

反应条件：

1.1 Reagents: Dimethylformamide , Triethylamine Catalysts: 4-(Dimethylamino)phenol Solvents: Dimethylformamide , Dichloromethane
1.2 Reagents: Triethylamine , tert-Butyldimethylsilyl chloride Catalysts: 4-(Dimethylamino)phenol Solvents: Dimethylformamide , Dichloromethane
2.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane
2.2 Reagents: Triethylamine Solvents: Dichloromethane

参考文献：

Thermal and catalyzed intramolecular Diels-Alder cyclizations of 2,8,10-undecatrienals

Marshall, James A.; et al, Journal of Organic Chemistry, 1987, 52(7), 1236-45

合成路线：1 步

反应条件：

1.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 10 min, -78 °C; 10 min, -78 °C
1.2 Solvents: Dichloromethane ; 10 min, -78 °C; 45 min, -78 °C
1.3 Reagents: Triethylamine ; 40 min, -78 °C; -78 °C → rt; 1 h, rt
1.4 Reagents: Sodium bicarbonate Solvents: Water ; rt

参考文献：

Unique Diastereoselectivity Trends in Aminyl Radical Cyclizations onto Silyl Enol Ethers

Zlotorzynska, Maria; et al, Journal of Organic Chemistry, 2010, 75(3), 864-872

合成路线：2 步

945223-74-5

反应条件：

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran
2.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride ; -78 °C
2.2 Reagents: Triethylamine ; -78 °C → rt

参考文献：

Discovery of substituted biphenyl imidazoles as potent, bioavailable bombesin receptor subtype-3 agonists

He, Shuwen; et al, Bioorganic & Medicinal Chemistry Letters, 2010, 20(6), 1913-1917

合成路线：2 步

64275-73-6

反应条件：

1.1 Reagents: Imidazole Catalysts: 4-(Dimethylamino)pyridine Solvents: Dimethylformamide ; rt → 0 °C; 0 °C; 0 °C → rt; 6 h, rt
2.1 Reagents: Sodium bicarbonate , Ozone Solvents: Methanol , Dichloromethane ; rt → -78 °C; 3.5 h, -78 °C
2.2 Reagents: Dimethyl sulfide ; -78 °C → rt

参考文献：

Syntheses of stereochemically diverse nine-membered ring-containing biaryls

Krishnan, Shyam; et al, Organic Letters, 2004, 6(22), 4021-4024

合成路线：2 步

821-41-0

参考文献：

A New Henry/Michael/Retro-Henry/Henry Domino Sequence Promoted by Bifunctional Organocatalysts

Quintavalla, Arianna; et al, Advanced Synthesis & Catalysis, 2013, 355(5), 938-946

合成路线：3 步

821-41-0