Gold-Catalyzed Tandem C−C and C−O Bond Formation:  A Highly Diastereoselective Formation of Cyclohex-4-ene-1,2-diol Derivatives

Lim, Choongmin; Kang, Ji Eun; Lee, Ji Eun; Shin, Seunghoon

doi:10.1021/ol071402f

Cited by 62 publications

(28 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Kozmin subsequently investigated the analogous intramolecular trapping by using substrates with tethered nucleophiles (i.e., 104 , R 2 = CH 2 OH) to form compounds such as 106 84. Shin recently extended this strategy to include intramolecular trapping by a carbonate ( 104 , R 3 = OBoc) 85. In the carbonate cyclization, Buchwald-type ligands provided superior catalyst reactivity compared to Ph 3 P.…”

Section: Cascade Reactions Initiated By Carbon Nucleophiles With πmentioning

confidence: 99%

Ligand Effects in Homogeneous Au Catalysis

2008

View full text Add to dashboard Cite

F. Dean Toste received his B.Sc. and M.Sc. degrees in chemistry from the University of Toronto where he worked with Prof. Ian W. J. Still. In 1995, he began his doctoral studies at Stanford University under the direction of Professor Barry M. Trost. Following postdoctoral studies with Professor Robert H. Grubbs at Caltech, he joined the faculty at the University of California, Berkeley, in 2002, and was promoted to Associate Professor in 2006. Current research in his group is aimed towards the design of catalysts and catalytic reactions and the application of these methods to chemical synthesis.

show abstract

Section: Cascade Reactions Initiated By Carbon Nucleophiles With πmentioning

confidence: 99%

Ligand Effects in Homogeneous Au Catalysis

2008

View full text Add to dashboard Cite

show abstract

“…For example, Shin and co-workers reported a valuable transformation using the tert -butoxycarbonyl (Boc) group to trap the cation following the activation of π-systems by gold in a route to cyclic carbonates (Scheme 10) [100]. The Boc-group was considered to be very effective at undergoing intramolecular nucleophilic attack of the cationic intermediate to gain access to highly functionalized cyclohex-4-ene-1,2-diol derivatives from simple 3-BocO-1,5-enynes.…”

Section: Reviewmentioning

confidence: 99%

When gold can do what iodine cannot do: A critical comparison

Hummel¹,

Kirsch²

2011

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryGold catalysis has emerged as one of the most dynamic fields in organic synthesis. Only recently, more and more domino processes, for which gold pre-catalysts were found to be outstandingly effective, were paralleled by employing iodine electrophiles in place of gold compounds. This review highlights how, in certain cases, iodonium activation can match gold-catalyzed reactions to construct identical product scaffolds. Likewise, processes are discussed where mostly identical starting materials are transformed into diverse frameworks depending on whether gold or iodonium activation was used to trigger the reaction.

show abstract

“…Echavarren has recently described a closely related protocol involving the 5-exo-cyclization/alkoxylation of 1,6-enynes catalyzed by cationic gold(I) complexes [130]. Shin has described the gold(I)-catalyzed tandem cyclization/acetoxylation of the tert-butyl carbonate derivatives of 1-hexen-5-yn-3-ols to form 4-cyclohexene-1,2-diol derivatives [131]. As a representative example, treatment of 90 with a catalytic 1 : 1 mixture of [P(t-Bu) 2 o-biphenyl]AuCl and AgSbF 6 led to isolation of cyclohexene 91 in 87% yield as an 8 : 1 mixture of diastereomers (Eq.…”

Section: Carboxylic Acid Derivatives As Nucleophilesmentioning

confidence: 99%

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

Widenhoefer

Song

2010

Catalyzed Carbon‐Heteroatom Bond Formation

View full text Add to dashboard Cite

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.

show abstract

Gold-Catalyzed Tandem C−C and C−O Bond Formation: A Highly Diastereoselective Formation of Cyclohex-4-ene-1,2-diol Derivatives

Cited by 62 publications

References 19 publications

Ligand Effects in Homogeneous Au Catalysis

Ligand Effects in Homogeneous Au Catalysis

When gold can do what iodine cannot do: A critical comparison

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

Contact Info

Product

Resources

About