Generation of 2-azaallyl anions by the transmetalation of N-(trialkylstannyl)methanimines. Pyrrolidine synthesis by [3 + 2] cycloadditions with alkenes

Pearson, William H.; Szura, Daniel P.; Postich, Michael J.

doi:10.1021/ja00030a031

Cited by 78 publications

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“…28 Alternatively, oxidation of the sulfide to a sulfone and reductive removal with sodium amalgam in alcoholic media accomplished the same transformation (not shown). For example, the phenylthio and phenylseleno groups may be removed reductively from 74 and 75 to provide pyrrolidines.…”

Section: Equationmentioning

confidence: 87%

“…28 When activated anionophiles such as stilbene or phenyl vinyl sulfide were present at the start of transmetalation, good yields of pyrrolidine cycloadducts were obtained. Ample precedent for the tin-lithium exchange of (2-azaallyl)stannanes can be found in the well-known transmetalations of allyl stannanes and α-amino stannanes.…”

Section: Scheme 11mentioning

confidence: 99%

“…For example, the phenylthio and phenylseleno groups may be removed reductively from 74 and 75 to provide pyrrolidines. 28,31,39 A Tamao-Fleming oxidation may be used to convert the vinyl silane-derived cycloadduct 77 to an alcohol. 40 Oxidation of the sulfide to a sulfoxide (e.g.…”

Section: Equationmentioning

confidence: 99%

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Cycloadditions of Nonstabilized2-Azaallyllithiums (2-Azaallyl Anions) and Azomethine Ylides withAlkenes: [3+2] Approaches to Pyrrolidinesand Application to Alkaloid Total Synthesis

Pearson¹,

Stoy²

2003

Synlett

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The [3+2] cycloaddition of 2-azaallyl anions with alkenes represents an attractive strategy for the synthesis of substituted pyrrolidines. Although cycloadditions of 2-azaallyl anions stabilized by aryl and ester groups have been known for more than three decades, only recently have versions bearing simply hydrogen or alkyl groups been discovered. These nonstabilized 2-azaallyl anions are generated by the low temperature transmetalation of (2azaallyl)stannanes with alkyllithiums. The resulting nonstabilized 2-azaallyllithiums undergo cycloaddition with certain alkenes and alkynes in both intra-and intermolecular modes to yield pyrrolidine or pyrroline cycloadducts. The methodology has been extended to 2-azapentadienyllithiums, heteroatom-substituted 2-azaallyllithiums, and polymer-supported 2-azaallyllithiums. Asymmetric 2azaallyl anion cycloadditions have also been investigated. Nonstabilized azomethine ylides may also be generated from (2-azaallyl)stannanes via an N-alkylation/destannylation or N-protonation/ destannylation sequence. Together, the cycloaddition of nonstabilized 2-azaallyllithiums and azomethine ylides with alkenes allows access to a broader range of pyrrolidines, since these species have complimentary reactivity profiles. 7.1.5 Approach to 6a-Epipretazettine 7.2 Intermolecular Cycloadditions 7.2.1 Lepadiformine Isomers 7.2.2 Lapidilectine B 7.2.3 Indolizidine 239CD 8 Commentary

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Section: Equationmentioning

confidence: 87%

Section: Scheme 11mentioning

confidence: 99%

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Cycloadditions of Nonstabilized2-Azaallyllithiums (2-Azaallyl Anions) and Azomethine Ylides withAlkenes: [3+2] Approaches to Pyrrolidinesand Application to Alkaloid Total Synthesis

Pearson¹,

Stoy²

2003

Synlett

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An efficient synthesis of 9,10-dihydro-9,10-(methaniminomethano)anthracene and several N-protected derivatives is described via the double reductive amination of cis-9,10-dihydro-9,10-dicarboxaldehyde.In the course of investigations into the generation of 2-azaallyl anions [1,2] via cycloreversions of N-metallated nitrogen-containing heterocycles, [3 -5] we

…”

mentioning

confidence: 99%

“…In the course of investigations into the generation of 2-azaallyl anions [1,2] via cycloreversions of N-metallated nitrogen-containing heterocycles, [3 -5] we…”

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confidence: 99%

The Synthesis of 9,10‐Dihydro‐9,10‐(Methaniminomethano)Anthracene andN‐Protected Derivatives Via Double Reductive Amination

Stoy

Rush

Pearson

2004

Synthetic Communications

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Anwendung der 2-Azaallylanionen-Cycloaddition in der enantioselektiven Totalsynthese von (+)-Coccinin

Pearson

Lian

1998

Angewandte Chemie

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Generation of 2-azaallyl anions by the transmetalation of N-(trialkylstannyl)methanimines. Pyrrolidine synthesis by [3 + 2] cycloadditions with alkenes

Cited by 78 publications

References 0 publications

Cycloadditions of Nonstabilized2-Azaallyllithiums (2-Azaallyl Anions) and Azomethine Ylides withAlkenes: [3+2] Approaches to Pyrrolidinesand Application to Alkaloid Total Synthesis

Cycloadditions of Nonstabilized2-Azaallyllithiums (2-Azaallyl Anions) and Azomethine Ylides withAlkenes: [3+2] Approaches to Pyrrolidinesand Application to Alkaloid Total Synthesis

The Synthesis of 9,10‐Dihydro‐9,10‐(Methaniminomethano)Anthracene andN‐Protected Derivatives Via Double Reductive Amination

Anwendung der 2-Azaallylanionen-Cycloaddition in der enantioselektiven Totalsynthese von (+)-Coccinin

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