Gold(I)-catalyzed enantioselective cycloaddition reactions
- Fernando López and
- José L. Mascareñas
Beilstein J. Org. Chem. 2013, 9, 2250–2264, doi:10.3762/bjoc.9.264
Graphical Abstract
Figure 1: Gold-promoted 1,2-acyloxy migration on propargylic systems.
Scheme 1: Gold-catalyzed enantioselective intermolecular cyclopropanation.
Scheme 2: Gold-catalyzed enantioselective intramolecular cyclopropanation.
Scheme 3: Gold-catalyzed cyclohepta-annulation cascade.
Scheme 4: Application to the formal synthesis of frondosin A.
Scheme 5: Gold(I)-catalyzed enantioselective cyclopropenation of alkynes.
Scheme 6: Enantioselective cyclopropanation of diazooxindoles.
Figure 2: Proposed structures for gold-activated allene complexes.
Scheme 7: Gold-catalyzed enantioselective [2 + 2] cycloadditions of allenenes.
Scheme 8: Gold-catalyzed allenediene [4 + 3] and [4 + 2] cycloadditions.
Scheme 9: Gold-catalyzed enantioselective [4 + 2] cycloadditions of allenedienes.
Scheme 10: Gold-catalyzed enantioselective [4 + 3] cycloadditions of allenedienes.
Scheme 11: Gold-catalyzed enantioselective [4 + 2] cycloadditions of allenamides.
Scheme 12: Enantioselective [2 + 2] cycloadditions of allenamides.
Scheme 13: Mechanistic rational for the gold-catalyzed [2 + 2] cycloadditions.
Scheme 14: Enantioselective cascade cycloadditions between allenamides and oxoalkenes.
Scheme 15: Enantioselective [3 + 2] cycloadditions of nitrones and allenamides.
Scheme 16: Enantioselective formal [4 + 3] cycloadditions leading to 1,2-oxazepane derivatives.
Scheme 17: Enantioselective gold(I)-catalyzed 1,3-dipolar [3 + 3] cycloaddition between 2-(1-alkynyl)-2-alken-...
Scheme 18: Enantioselective [4 + 3] cycloaddition leading to 5,7-fused bicyclic furo[3,4-d][1,2]oxazepines.
Recent developments in gold-catalyzed cycloaddition reactions
- Fernando López and
- José L. Mascareñas
Beilstein J. Org. Chem. 2011, 7, 1075–1094, doi:10.3762/bjoc.7.124
Graphical Abstract
Scheme 1: AuCl3-catalyzed benzannulations reported by Yamamoto.
Scheme 2: Synthesis of 9-oxabicyclo[3.3.1]nona-4,7-dienes from 1-oxo-4-oxy-5-ynes [40].
Scheme 3: Stereocontrolled oxacyclization/(4 + 2)-cycloaddition cascade of ketone–allene substrates [43].
Scheme 4: Gold-catalyzed synthesis of polycyclic, fully substituted furans from 1-(1-alkynyl)cyclopropyl keto...
Scheme 5: Gold-catalyzed 1,3-dipolar cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with nitrones [47].
Scheme 6: Enantioselective 1,3-dipolar cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with nitrones [48].
Scheme 7: Gold-catalyzed 1,3-dipolar cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with α,β-unsaturated imine...
Scheme 8: Gold-catalyzed (4 + 3) cycloadditions of 1-(1-alkynyl)oxiranyl ketones [50].
Scheme 9: (3 + 2) Cycloaddition of gold-containing azomethine ylides [52].
Scheme 10: Gold-catalyzed generation and reaction of azomethine ylides [53].
Scheme 11: Gold-catalyzed intramolecular (4 + 2) cycloadditions of unactivated alkynes and dienes [55].
Scheme 12: Gold-catalyzed preparation of bicyclo[4.3.0]nonane derivatives from dienol silyl ethers [59].
Scheme 13: Gold(I)-catalyzed intramolecular (4 + 2) cycloadditions of arylalkynes or 1,3-enynes with alkenes [60].
Scheme 14: Gold(I)-catalyzed intermolecular (2 + 2) cycloaddition of alkynes with alkenes [62].
Scheme 15: Metal-catalyzed cycloaddition of alkynes tethered to cycloheptatriene [65].
Scheme 16: Gold-catalyzed cycloaddition of functionalized ketoenynes: Synthesis of (+)-orientalol F [68].
Scheme 17: Gold-catalyzed intermolecular cyclopropanation of enynes with alkenes [70].
Scheme 18: Gold-catalyzed intermolecular hetero-dehydro Diels–Alder cycloaddition [72].
Figure 1: Gold-catalyzed 1,2- or 1,3-acyloxy migrations of propargyl esters.
Scheme 19: Gold(I)-catalyzed stereoselective olefin cyclopropanation [74].
Scheme 20: Reaction of propargylic benzoates with α,β-unsaturated imines to give azepine cycloadducts [77].
Scheme 21: Gold-catalyzed (3 + 3) annulation of azomethine imines with propargyl esters [81].
Scheme 22: Gold(I)-catalyzed isomerization of 5-en-2-yn-1-yl acetates [83].
Scheme 23: (3 + 2) and (2 + 2) cycloadditions of indole-3-acetates 41 [85,86].
Scheme 24: Gold(I)-catalyzed (2 + 2) cycloaddition of allenenes [87].
Scheme 25: Formal (3 + 2) cycloaddition of allenyl MOM ethers and alkenes [90].
Scheme 26: (4 + 3) Cycloadditions of allenedienes [97,98].
Scheme 27: Gold-catalyzed transannular (4 + 3) cycloaddition reactions [101].
Scheme 28: Gold(I)-catalyzed (4 + 2) cycloadditions of allenedienes [102].
Scheme 29: Enantioselective gold(I)-catalyzed (4 + 2) cycloadditions of allenedienes [88,102,104].
Scheme 30: (3 + 2) versus (2 + 2) Cycloadditions of allenenes [87,99].
Figure 2: NHC ligands with different π-acceptor properties [106].
Scheme 31: (3 + 2) versus (2 + 2) Cycloadditions of allenenes [106].
Scheme 32: Gold(I)-catalyzed intermolecular (4 + 2) cycloaddition of allenamides and acyclic dienes [109].
