An alternative approach to the synthesis of the carbapenam ring system. Allenes as acceptor-donor reagents in 3 + 2 annelations

Mastalerz, Harold; Vinet, V.

doi:10.1016/s0040-4039(00)98722-7

Cited by 8 publications

(2 citation statements)

References 12 publications

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“…The allene 414 was generated in situ and functioned as an acceptor−donor synthon when reacted with β-lactam 415 . Cyclization by intramolecular alkylation furnished the desired carbapenem 416 after sulfoxide elimination . Dienyl sulfone 417 , as well as other activated dienes, underwent conjugate addition of the sulfoxonium ylide 418 , followed by intramolecular displacement of dimethyl sulfoxide, affording the corresponding cyclopentene .…”

Section: Tandem Conjugate Additions and Intramolecular Alkylations Or...mentioning

confidence: 99%

“…Cyclization by intramolecular alkylation furnished the desired carbapenem 416 after sulfoxide elimination. 315 Dienyl sulfone 417, as well as other activated dienes, underwent conjugate addition of the sulfoxonium ylide 418, followed by intramolecular displacement of dimethyl sulfoxide, affording the corresponding cyclopentene. 316 Aldehydes can also serve as the electrophilic components in the cyclization step.…”

Section: Allenic and Dienyl Sulfonesmentioning

confidence: 99%

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Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones

2010

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Introduction 4499 2. Diels-Alder Cycloadditions 4499 2.1. Unsaturated Sulfones as Dienophiles 4499 2.1.1. Early Studies 4499 2.1.2. Aromatization of Cycloaddition Products of Acetylenic Sulfones 4501 2.1.3. Iterative Diels-Alder and Ramberg-Backlund Reactions of Chloroalkylsulfonyl Allenes 4502 2.1.4. Diels-Alder Cycloadditions of Bis(sulfonyl)acetylenes and Their Equivalents 4502 2.1.5. Diels-Alder Cycloadditions of Acetylenic Sulfones Containing Heteroatom Substituents 4503 2.1.6. Diels-Alder Reactions of Dienyl Sulfones as Dienophiles 4504 2.1.7. Diels-Alder Reactions of Unsaturated Sulfones with Pyrroles 4505 2.1.8. Diels-Alder Reactions of Unsaturated Sulfones with Furans and Isobenzofurans 4507 2.1.9. Miscellaneous Cycloadditions 4508 2.2. Dienyl Sulfones As the Diene Components in Diels-Alder Reactions 4509 2.2.1. 1-Sulfonyl Derivatives † Dedicated to Professor David N. Harpp, for his inspiring contributions as a teacher, mentor and scholar.

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Section: Tandem Conjugate Additions and Intramolecular Alkylations Or...mentioning

confidence: 99%

Section: Allenic and Dienyl Sulfonesmentioning

confidence: 99%