Transfer of Chirality in Radical Cyclizations. Cyclization of <i>o</i>-Haloacrylanilides to Oxindoles with Transfer of Axial Chirality to a Newly Formed Stereocenter

Curran, Dennis P.; Liu, and Weidong; Chen, Christine Hiu-Tung

doi:10.1021/ja993329x

Cited by 104 publications

(34 citation statements)

References 27 publications

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“…As a related example, transfer of chirality was also investigated in radical cyclization by Curran's group (Scheme ) 9. In this unique cyclization procedure, axial chirality was transferred into a new stereocenter with retention of chirality as a result of the almost complete absence of racemization of radical intermediates.…”

Section: Enantioselective Radical Cyclizationsmentioning

confidence: 99%

Enantioselective Radical Cyclizations: A New Approach to Stereocontrol of Cascade Reactions

Miyabe

Takemoto

2007

Chemistry A European J

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Stereocontrol in a cascade radical addition-cyclization-trapping reaction was achieved by a new approach, which utilizes a hydroxamate ester moiety as a coordinating chiral Lewis acid tether between two radical acceptors. A remarkable feature of this reaction is the construction of three bonds and tertiary and quaternary stereogenic centers through both inter- and intramolecular carbon-carbon bond-forming processes. The chiral Lewis acid mediated reaction of oxime ethers also proceeded smoothly with good enantio- and diastereoselectivities, indicating the usefulness of the cascade approach for the asymmetric synthesis of various gamma-lactams.

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Section: Enantioselective Radical Cyclizationsmentioning

confidence: 99%

Enantioselective Radical Cyclizations: A New Approach to Stereocontrol of Cascade Reactions

Miyabe

Takemoto

2007

Chemistry A European J

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“…Curran et al reported cyclization of acrylanilide derivatives to oxindoles [35]. In this reaction, an axial-to-central chirality is taking place [36].…”

Section: Aryl Radicalsmentioning

confidence: 99%

Memory of chirality in reactions involving monoradicals

Gloor

Dénès

Renaud

2016

Free Radical Research

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The effects of memory of chirality (MoC) in reactions involving monoradical species are reviewed here. Reactions involving a nonracemic chiral starting material bearing a single stereogenic element such as a chiral center or chiral axis directly involved in the new bond formation are discussed. These reactions lead to a nonracemic product via an intermediate susceptible to rapid racemization. Memory of chirality has been observed in cyclic radicals, aryl, ester/amide substituted acyclic radicals, and benzylic radicals at temperatures up to 130 °C.

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“…Sibi and coworkers have developed an interesting template which contains a nitrogen fluxional group that can work in conjunction with a chiral ligand (Scheme 35) [92]. Using a small chiral bisoxazoline ligand (136), excellent ee's for product 135 can be obtained when the fluxional nitrogen substituent is Scheme 35 Fluxional template for radical enantioselective conjugate additions large (see entries 1-3). Interestingly, by selecting the proper Lewis acid it was found that enantiomeric products could be produced in near optically pure form (compare entries 4 and 5; 6 and 7).…”

Section: Conjugate Additionmentioning

confidence: 99%

“…A unique cyclization procedure was conducted by Curran et al in which they showed that axial chirality can be transferred into a new stereocenter with retention of chirality (Scheme 46) [136]. Substrates M or P-174a,b…”

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confidence: 99%