[3+2]‐Anionic Electrocyclization Using 2,3‐Bis(Phenylsulfonyl)‐1,3‐Butadiene: trans‐4,7,7‐Tricarbomethoxy‐2‐Phenylsulfonylbicyclo[3.3.0]Oct‐1‐Ene

Padwa, Albert; Watterson, S. H.; Ni, Zhi‐Jie

doi:10.1002/0471264180.os074.16

Cited by 1 publication

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“…A more recent cascade strategy that we are currently applying to the synthesis of various piperidine alkaloids is founded on a renewed interest in the conjugate additiondipolar cycloaddition cascade that my group had previously used to prepare 2-substituted-4-piperidones. 78 This cascade utilizes 2,3-bis(phenylsulfonyl)-1,3-butadiene (184) 79 as a key reactant which functions as both a Michael acceptor and a dipolarophile. Thus, conjugate addition of an oxime to diene 184 followed by proton transfer creates a transient nitrone 185 that undergoes a 1,3-dipolar cycloaddition with the tethered vinyl sulfone (Scheme 40).…”

Section: Tandem Michael Addition/dipolar Cycloaddition Cascadementioning

confidence: 99%

A Chemistry Cascade: From Physical Organic Studies of Alkoxy Radicals to Alkaloid Synthesis

Padwa

2009

J. Org. Chem.

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In this Perspective, I present a personal account of a succession of chemical projects that I was involved with, each of which triggered or initiated my next research undertaking. It started with my early work in the field of physical organic photochemistry, which, in turn, guided me to my current research dealing with the synthesis of biologically active alkaloids. The article highlights some of the dominant themes of my research program over the past 48 years. Subject matter that is discussed includes the generation of reactive intermediates by photoexcitation, [1,3]-dipolar cycloaddition chemistry, rhodium(II)-catalyzed domino reactions of alpha-diazo carbonyl compounds, intramolecular [4 + 2]-cycloaddition of 2-amidofurans, and the utilization of various thio fragments for the synthesis of nitrogen heterocycles.

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Section: Tandem Michael Addition/dipolar Cycloaddition Cascadementioning

confidence: 99%