Nickel-catalyzed intramolecular [4 + 2] dienyne cycloadditions: an efficient new method for the synthesis of polycycles containing cyclohexa-1,4-dienes

Wender, Paul A.; Jenkins, Thomas E.

doi:10.1021/ja00198a071

Cited by 157 publications

(53 citation statements)

References 1 publication

(1 reference statement)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[1] For instance, nickel-catalyzed [4+4], [2] [4+2], [3] and [2+2+2] [4] cycloadditions have received considerable attention. Other important nickel-catalyzed processes include olefin polymerizations, [2b, 5] dimerizations, [1a, 6] hydrocyanations, [7] and hydrometallations.…”

Section: Introductionmentioning

confidence: 99%

Nickel‐Catalyzed Reductive Cyclizations and Couplings

2004

View full text Add to dashboard Cite

For over 50 years, nickel catalysis has been applied in cycloaddition processes. Nickel-catalyzed reductive couplings and cyclizations, however, have only recently attracted a high level of interest. This group of new reactions allows a broad range of multicomponent couplings involving two or more pi components with a main-group or transition-metal reagent. These processes allow the assembly of important organic substructures from widely available reaction components. Multiple contiguous stereocenters, polycyclic ring systems, and novel arrays of complex functionality may often be prepared from simple, achiral, acyclic precursors. With three or more reactive functional groups participating in the catalytic processes, many mechanistic questions abound, including the precise timing of bond constructions and the nature of reactive intermediates. This Review is thus aimed at providing a critical evaluation of recent progress in this rapidly developing field.

show abstract

Section: Introductionmentioning

confidence: 99%

Nickel‐Catalyzed Reductive Cyclizations and Couplings

2004

View full text Add to dashboard Cite

show abstract

“…As is the case for other cyclooligomerization and co-cyclooligomerization reactions, the selective formation of carbocyclic compounds is accomplished by means of a nickel-catalyzed intramolecular co-cycloisomerization of dienes [56,57]. For example, the thermally forbidden nickel-catalyzed intramolecular [4þ4] cycloaddition of dienes is effected by the Ni (0) The intramolecular [4þ2] cycloaddition of o-dienynes [57] is a thermally permitted process and proceeds at elevated temperatures (e.g., 180-200 C).…”

Section: 44mentioning

confidence: 99%

Cyclooligomerization and Cycloisomerization of Alkenes and Alkynes

Saito¹

2005

Modern Organonickel Chemistry

View full text Add to dashboard Cite

Nickel-catalyzed cyclooligomerization and cycloisomerization reactions of alkenes and alkynes form the cornerstones of organic transition metal chemistry (Reppe, in the 1940s; see Section 6.3.1), and so far these have been among the main subjects studied extensively. In this chapter, nickel-catalyzed cyclooligomerization and cycloisomerization reactions will be described, as will certain nickel-mediated (stoichiometric) reactions, which are closely related to the catalytic reactions. Emphasis is placed on recent developments in nickel chemistry, as earlier studies have been repeatedly reviewed from several viewpoints [1-10]. Cyclization and cycloaddition reactions which involve the addition of other substrates (e.g., hydrosilanes, hydrostannanes and disilanes) will be described in other appropriate chapters in this monograph. 6.1 Cyclooligomerization of AlkenesIn nickel-catalyzed cyclooligomerization reactions of alkenes, strained compounds such as cyclopropenes, methylenecyclopropanes, and norbornadiene are normally used as the reactive substrates. The reactions may involve either the cleavage of the weakened carbon-carbon p bond -as is the case for many cyclooligomerization and cycloisomerization reactions -or the cleavage of the strained carbon-carbon s bond, which is followed by the formation of new carbon-carbon s bonds. Unstrained alkenes usually produce linear oligomers in the presence of nickel catalysts (see Chapter 3).Cyclopropenes are highly strained carbocyclic compounds. For example, the calculated strain energy of cyclopropene is 228 KJ mol À1 (54.5 Kcal mol À1 ) [10]. Accordingly, cyclopropenes are prone to undergo cyclooligomerization in the presence of a Ni catalyst. As an example, 3,3-dimethylcyclopropene provides cyclodimerization and cyclotrimerization products (Eq. (6.1)) [11a, b]. A generally accepted mechanism for this reaction is shown in Scheme 6.1, where the Ni(0) complex interacts with the p bond of the cyclopropene molecule and forms a Ni(0)-h 2 -olefin Modern Organonickel Chemistry. Edited by Y. Tamaru

show abstract

“…For instance, nickel-catalyzed [4 + 4], [4 + 2], and [2 + 2 + 2] cycloadditions have received considerable attention. [11,12] Over the past decade, nickel-catalyzed reductive cyclizations and couplings have evolved into a broadly useful strategy for assembling synthetically versatile substructures and complex molecules. [13] Moreover, chiral nickel complexes are becoming potential practical catalysts in enantioselective transformations.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of β‐Hydroxy‐α‐Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α‐Isothiocyanato Imide with Aldehydes

Chen

Zhu

Qiao

et al. 2010

Chemistry A European J

View full text Add to dashboard Cite

An easily available and efficient chiral N,N'-dioxide-nickel(II) complex catalyst has been developed for the direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes which produces the products in morderate to high yields (up to 98 %) with excellent diastereo- (up to >99:1 d.r.) and enantioselectivities (up to >99 % ee). A variety of aromatic, heteroaromatic, alpha,beta-unsaturated, and aliphatic aldehydes were found to be suitable substrates in the presence of 2.5 mol % L-proline-derived N,N'-dioxide L5-nickel(II) complex. This process was air-tolerant and easily manipulated with available reagents. Based on experimental investigations, a possible transition state has been proposed to explain the origin of reactivity and asymmetric inductivity.

show abstract

Nickel-catalyzed intramolecular [4 + 2] dienyne cycloadditions: an efficient new method for the synthesis of polycycles containing cyclohexa-1,4-dienes

Cited by 157 publications

References 1 publication

Nickel‐Catalyzed Reductive Cyclizations and Couplings

Nickel‐Catalyzed Reductive Cyclizations and Couplings

Cyclooligomerization and Cycloisomerization of Alkenes and Alkynes

Efficient Synthesis of β‐Hydroxy‐α‐Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α‐Isothiocyanato Imide with Aldehydes

Contact Info

Product

Resources

About