Memory of chirality in reactions involving monoradicals

References

• Kawabata T, Yahiro K, Fuji K. Memory of chirality: enantioselective alkylation reactions at an asymmetric carbon adjacent to a carbonyl group. J Am Chem Soc 1991;113:9694–9696.
   Web of Science ®Google Scholar
• Seebach D, Wasmuth D. Alkylierung von aminosäuren ohne verlust der optischen aktivität: α- und β-alkylierung eines asparaginsäure-derivates. Angew Chem 1981;93:1007–1008.
   Google Scholar
• Leuchs H. Die stereochemische behandlung der keto-enol-frage. (Über Spirane IV). Chem Ber 1913;46:2435–2442.
   Google Scholar
• Luche MJ, Marquet A, Snatzke G. Configuration absolue d'indanones-1 et tetralones-1 substituees en 2. Tetrahedron 1972;28:1677–1695.
   Web of Science ®Google Scholar
• Ronteix MJ, Marquet A. Retention d'activite optique lors de l'halogenation de cetones optiquement actives. Tetrahedron Lett 1966;7:5801–5806.
   Google Scholar
• Jones WM. Pyrazolines. IV. On the mechanism of decomposition and conformational analyses of 2-pyrazolines 1. J Am Chem Soc 1960;82:3136–3137.
   Web of Science ®Google Scholar
• Rinehart KL, Van Auken TV. Light-induced decomposition of pyrazolines. An improved entry into the cyclopropane series. J Am Chem Soc 1960;82:5251.
   Web of Science ®Google Scholar
• Orban I, Schaffner K, Jeger O. On the photochemical cyclization of saturated ketones and aldehydes to cyclobutanols. J Am Chem Soc 1963;85:3033–3035.
   Web of Science ®Google Scholar
• Fuji K, Kawabata T. Memory of chirality – a new principle in enolate chemistry. Chem-Eur J 1998;4:373–376.
   Google Scholar
• Matsumura Y, Shirakawa Y, Satoh Y, Umino M, Tanaka T, Maki T, Onomura O. First example of memory of chirality in carbenium ion chemistry. Org Lett 2000;2:1689–1691.
   PubMed Web of Science ®Google Scholar
• Heiba EAI, Dessau RM. Vinyl radical isomerization. II. A new free-radical synthesis of γ-lactones with retention of optical activity. J Am Chem Soc 1967;89:2238–2239.
   Web of Science ®Google Scholar
• Crich D, Shirai M, Brebion F, Rumthao S. Enantioselective alkene radical cations reactions. Tetrahedron 2006;62:6501–6518.
   Web of Science ®Google Scholar
• Zhao H, Hsu DC, Carlier PR. Memory of chirality: An emerging strategy for asymmetric synthesis. Synthesis 2005;(1):1–16. doi: 10.1055/s-2004-834931.
   Web of Science ®Google Scholar
• Alezra V, Kawabata T. Recent progress in memory of chirality (MOC): an advanced chiral pool. Synthesis 2016.
   Web of Science ®Google Scholar
• Mu Y, Zhu C, Shi Z. Memory of chirality (MOC) in intramolecular sp3 C-H Amination. Synlett 2016;27:486–492.
   Web of Science ®Google Scholar
• Cozzi F, Siegel JS. Chirony of stereochemical metaphors. Org Biomol Chem 2005;3:4296–4298.
   PubMed Web of Science ®Google Scholar
• Curran DP, Porter NA, Giese B. Stereochemistry of radical reactions: concepts, guidelines, and synthetic applications. Weinheim; New York: VCH; 1996.
   Google Scholar
• Paddon-Row MN, Houk KN. Conformational dependence of the pyramidalization of alkyl radicals. J Phys Chem-US 1985;89:3771–3774.
   Web of Science ®Google Scholar
• Griller D, Ingold KU, Krusic PJ, Fischer H. On the configuration of the tert-butyl radical [2]. J Am Chem Soc 1978;100:6750–6752.
   Web of Science ®Google Scholar
• Ignaczak A. Comparative quantum study on tert-butyl radical and cation. J Theoret Comput Chem 2011;10:325–348.
   Web of Science ®Google Scholar
• El Blidi L, Nechab M, Vanthuyne N, Gastaldi S, Bertrand MP, Gil G. En route to (S)-selective chemoenzymatic dynamic kinetic resolution of aliphatic amines. One-pot KR/racemization/KR sequence leading to (S)-amides. J Org Chem 2009;74:2901–2903.
   PubMed Web of Science ®Google Scholar
• Walborsky HM. The cyclopropyl radical. Tetrahedron 1981;37:1625–1651.
   Web of Science ®Google Scholar
• Ando T, Yamanaka H, Namigata F, Funasaka W. Reduction of gem-halofluorocyclopropanes with tributyltin hydride. J Org Chem 1970;35:33–38.
   Web of Science ®Google Scholar
• Gawronska K, Gawronski J, Walborsky HM. Formation of a chiral 1-fluoro-2,2-diphenylcyclopropyl radical in the Barton decarboxylation reaction. J Org Chem 1991;56:2193–2197.
   Web of Science ®Google Scholar
• Walborsky HM, Collins PC. Cyclopropanes. XXXVIII. Effect of 1-substituents on the stereochemical stability of the cyclopropyl radical. J Org Chem 1976;41:940–946.
   Web of Science ®Google Scholar
• Walborsky HM, Aronoff MS. Cyclopropanes XXXIII. Reaction of lithium metal surfaces with optically active 1-halo-1-methyl-2,2-diphenylcyclopropane. J Organomet Chem 1973;51:55–75.
   Web of Science ®Google Scholar
• Walborsky HM, Aronoff MS. Cyclopropanes XIX. Reaction of lithium metal with optically active halides. J Organomet Chem 1965;4:418–420.
   Web of Science ®Google Scholar
• Walborsky HM, Johnson FP, Pierce JB. Cyclopropanes. XXIV. Sodium-liquid ammonia reduction of optically active cyclopropyl halides. J Am Chem Soc 1968;90:5222–5225.
   Web of Science ®Google Scholar
• Boche G, Schneider DR, Wintermayr H. Alternative pathways in the reactions of cyclopropyl halides with alkali metal naphthalenes. J Am Chem Soc 1980;102:5697–5699.
   Web of Science ®Google Scholar
• Buckmelter AJ, Powers JP, Rychnovsky SD. Nonequilibrium radical reductions. J Am Chem Soc 1998;120:5589–5590.
   Web of Science ®Google Scholar
• Giese B, Dupuis J. Anomeric effect of radicals. Tetrahedron Lett 1984;25:1349–1352.
   Web of Science ®Google Scholar
• Rychnovsky SD, Hata T, Kim AI, Buckmelter AJ. Use of a conformational radical clock for evaluating alkyllithium-mediated cyclization reactions. Org Lett 2001;3:807–810.
   PubMed Web of Science ®Google Scholar
• Buckmelter AJ, Kim AI, Rychnovsky SD. Conformational memory in enantioselective radical reductions and a new radical clock reaction. J Am Chem Soc 2000;122:9386–9390.
   Web of Science ®Google Scholar
• Dalgard JE, Rychnovsky SD. Memory of chirality in the transannular cyclization of cyclodecenyl radicals. Org Lett 2004;6:2713–2716.
   PubMed Web of Science ®Google Scholar
• Curran DP, Liu W, Chen CHT. Transfer of chirality in radical cyclizations. Cyclization of o- haloacrylanilides to oxindoles with transfer of axial chirality to a newly formed stereocenter. J Am Chem Soc 1999;121:11012–11013.
   Web of Science ®Google Scholar
• Campolo D, Gastaldi S, Roussel C, Bertrand MP, Nechab M. Axial-to-central chirality transfer in cyclization processes. Chem Soc Rev 2013;42:8434.
   PubMed Web of Science ®Google Scholar
• Curran DP, Chen CHT, Geib SJ, Lapierre AJB. Asymmetric radical cyclization reactions of axially chiral N-allyl-o-iodoanilides to form enantioenriched N-acyl dihydroindoles. Tetrahedron 2004;60:4413–4424.
   Web of Science ®Google Scholar
• Petit M, Geib SJ, Curran DP. Asymmetric reactions of axially chiral amides: use of removable ortho-substituents in radical cyclizations of o-iodoacrylanilides and N-allyl-N-o-iodoacrylamides. Tetrahedron 2004;60:7543–7552.
   Web of Science ®Google Scholar
• Guthrie DB, Curran DP. Asymmetric radical and anionic cyclizations of axially chiral carbamates. Org Lett 2009;11:249–251.
   PubMed Web of Science ®Google Scholar
• Bruch A, Ambrosius A, Fröhlich R, Studer A, Guthrie DB, Zhang H, Curran DP. Memory of axial chirality in aryl radical phosphanylations. J Am Chem Soc 2010;132:11452–11454.
   PubMed Web of Science ®Google Scholar
• Sasmal A, Taniguchi T, Wipf P, Curran DP. Memory of chirality in rebound cyclizations of α-amide radicals. Can J Chem 2013;91:1–5.
   Web of Science ®Google Scholar
• Quirante J, Diaba F, Vila X, Bonjoch J, Lago E, Molins E. An unexpected course in the 6-exo radical cyclizations of trichloroacetamides on changing the N-substituent from benzyl to α-methylbenzyl. Comptes Rendus de l'Academie des Sciences - Series IIc: Chemistry. 2001;4:513–521.
   Web of Science ®Google Scholar
• Diaba F, Montiel JA, Bonjoch J. Unusual rearrangement and dearomatization reactions in Cu(I)-catalyzed atom transfer radical cyclizations from N-(1-phenylethyl)trichloroacetamides. Tetrahedron 2013;69:4883–4889.
   Web of Science ®Google Scholar
• Amaoka Y, Kamijo S, Hoshikawa T, Inoue M. Radical amination of C(sp3)-H bonds using N-hydroxyphthalimide and dialkyl azodicarboxylate. J Org Chem 2012;77:9959–9969.
   PubMed Web of Science ®Google Scholar
• Schmalz HG, De Koning CB, Bernicke D, Siegel S, Pfletschinger A. Memory of chirality in electron transfer mediated benzylic umpolung reactions of arene - Cr(CO)3 complexes. Angew Chem Int Edit 1999;38:1620–1623.
   Web of Science ®Google Scholar
• Porter NA, Mills KA, Caldwell SE, Dubay GR. The mechanism of the [3,2] allylperoxyl rearrangement: a radical-dioxygen pair reaction that proceeds with stereochemical memory. J Am Chem Soc 1994;116:6697–6705.
   Web of Science ®Google Scholar