Gold‐ or Platinum‐Catalyzed Tandem Cycloisomerization/Prins‐Type Cyclization Reactions

Barluenga, José; Diéguez, Alejandro; Fernández, Amadeo; Rodríguez, Félix; Fañanás, Francisco J.

doi:10.1002/anie.200503874

Cited by 143 publications

(40 citation statements)

References 22 publications

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“…Cycloisomerization of 6 to 7 a: Methylene chloride (10 mL) was added to a mixture of gold complex [Au{P(C 6 F 5 ) 3 }Cl] (5.1 mg, 0.0067 mmol) and AgSbF 6 (2.3 mg, 0.0067 mmol), and the reaction mixture was stirred for 10 min. The resulting solution was filtered through a pad of celite and concentrated.…”

Section: Methodsmentioning

confidence: 99%

Gold(I)‐Catalyzed Cycloisomerization of 3‐Methoxy‐1,6‐enynes Featuring Tandem Cyclization and [3,3]‐Sigmatropic Rearrangement

et al. 2008

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Golden reactivity: A new gold(I)‐catalyzed cycloisomerization of 3‐methoxy‐1,6‐enynes was discovered. Structurally simple 3‐methoxy‐1,6‐enynes engage in a tandem cyclization/[3,3]‐sigmatropic rearrangement to deliver a variety of 1‐methoxy‐1,4‐cycloheptadienes (see scheme). Notably, the reaction can be performed under very mild conditions and the synthetic utility of this reaction was demonstrated by facile conversion of the product into various cyclohept‐4‐en‐1‐ones.

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Section: Methodsmentioning

confidence: 99%

Gold(I)‐Catalyzed Cycloisomerization of 3‐Methoxy‐1,6‐enynes Featuring Tandem Cyclization and [3,3]‐Sigmatropic Rearrangement

et al. 2008

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“…Many of the products obtained are highly useful in natural products synthesis. (35) The reaction occurs with complete chirality transfer and very high diastereoselectivity for the free primary amine. However, if X = Boc or Ac, the diastereoselectivity is decreased.…”

Section: Tandem Reactions Involving Friedel-crafts Type Additionmentioning

confidence: 99%

Gold(III) Chloride

Coghlan

Nguyen

et al. 2015

Encyclopedia of Reagents for Organic Synthesis

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“…Li has described a gold(III)-catalyzed protocol for the annulation of salicylicaldehydes with aryl acetylenes to form isoflavanones [23]. Barluenga has reported the gold(III)-catalyzed tandem cycloisomerization/Prins-type cyclization of v-alkynols that possess an appropriately positioned alkenyl group to form eight-membered carbocycles [24]. As an example, treatment of diallyl v-alkynol 10 with a catalytic amount of AuCl 3 in propanol at 80 C for 12 h led to isolation of bicyclic ether 11 in 94% yield (Eq.…”

Section: Tandem Cào/càc Bond Forming Processesmentioning

confidence: 99%

Gold‐Catalyzed Addition of Oxygen Nucleophiles to CC Multiple Bonds

Widenhoefer

Song

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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The direct, catalytic addition of an oxygen nucleophile to a CÀC multiple bond represents an attractive approach to the formation of CÀO bonds from simple, readily available precursors. For this reason, there has been considerable interest in the identification of new and effective catalysts for the addition of oxygen nucleophiles to CÀC multiple bonds. One of the most significant developments in homogenous catalysis over the past 5-10 years has been the emergence of soluble gold complexes as catalysts for organic transformations [1]. Although a number of synthetically useful transformations have been developed, gold complexes have demonstrated particular utility as catalysts for the functionalization of CÀC multiple bonds with heteroatom nucleophiles, including oxygen nucleophiles such as water, carbinols, carbonyl compounds, and ethers. Early efforts in this area focused primarily on the application of simple gold(III) salts as catalysts, but interest has increasingly shifted toward the application of cationic gold(I) complexes supported by a phosphine or N-heterocyclic carbene ligands as catalysts for CÀO bond formation. These cationic gold(I) complexes are electrophilic, highly carbophilic compounds that are particularly suitable for p-activation catalysis. Herein we review the application of soluble gold(I) and gold(III) complexes as catalysts for the addition of oxygen nucleophiles to CÀC multiple bonds through 2008. This review is restricted to transformations that involve addition of an oxygen nucleophile to an electronically unactivated CÀC multiple bond catalyzed by a well-defined, soluble gold species.

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Gold‐ or Platinum‐Catalyzed Tandem Cycloisomerization/Prins‐Type Cyclization Reactions

Abstract: Straightforward and efficient: Functionalized eight‐membered carbocycles are easily obtained from simple allyl‐substituted 5‐hexyn‐1‐ol derivatives by a catalytic tandem sequence involving a 6‐exo cycloisomerization followed by a Prins‐type cyclization (see scheme).

Cited by 143 publications

References 22 publications

Gold(I)‐Catalyzed Cycloisomerization of 3‐Methoxy‐1,6‐enynes Featuring Tandem Cyclization and [3,3]‐Sigmatropic Rearrangement

Gold(I)‐Catalyzed Cycloisomerization of 3‐Methoxy‐1,6‐enynes Featuring Tandem Cyclization and [3,3]‐Sigmatropic Rearrangement

Gold(III) Chloride

Gold‐Catalyzed Addition of Oxygen Nucleophiles to CC Multiple Bonds

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