ACS Combinatorial Science
Technology Note
Three Step One-Pot Synthesis of a Novel 2,3,5-Substituted Pyrazine
Library. ACS Comb. Sci. 2011, 13, 449−452. (c) El-Dahshan, A.;
Ahsanullah; Rademann. Efficient Access to Peptidyl Ketones and
Peptidyl Diketones via C-Alkylations and C-Acylations of Polymer-
Supported Phosphorus Ylides Followed by Hydrolytic and/or
Oxidative Cleavage. Biopolymers 2010, 94, 220−228. (d) Christoforou,
I. C.; Kalogirou, A. S.; Koutentis, P. A. The Preparation of Dicyano-
1,3,4-Thiadiazole and Tricyanothiazole via 1,2,3-Dithiazole Chemistry.
Tetrahedron 2009, 65, 9967−9972. (e) Comely, A. C.; Gibson, S. E.;
Hales, N. J. Polymer-Supported Cobalt Carbonyl Complexes as Novel
Solid-Phase Catalysts of the Pauson−Khand Reaction. Chem. Commun.
2000, 305−306. (f) Tunoori, A. R.; Dutta, D.; Georg, G. I. Polymer-
Bound Triphenylphosphine as Traceless Reagent for Mitsunobu
Reactions in Combinatorial Chemistry: Synthesis of Aryl Ethers from
Phenols and Alcohols. Tetrahedron Lett. 1998, 39, 8751−8754.
(g) Classon, B.; Liu, Z. New Halogenations Reagent Systems Useful
for the Mild One-step Conversion of Alcohols into Iodides or
Bromides. J. Org. Chem. 1988, 53, 6126−6130. (h) Holletz, T.; Cech,
D. A Facile Procedure for the Reduction of Azido Nucleosides to
Amines Using Polymer Bound Triphenylphosphine. Synthesis 1994,
1994, 789−791.
(5) Regen, S. L.; Lee, D. P. Solid Phase Phosphorous Reagents.
Conversion of Alcohols to Alkyl Chlorides. J. Org. Chem. 1975, 40,
1669−1670.
(6) Otera, J. Esterification Methods, Reactions and Applications; Wiley-
VCH: Weinheim, Germany, 2003.
(7) Tian, J.; Gao, W.-C.; Zhou, D.-M.; Zhang, C. Recyclable
Hypervalent Iodine (III) Reagent Iodosodilactone as an Efficient
Coupling Reagent for Direct Esterification, Amidation, and Peptide
Coupling. Org. Lett. 2012, 14, 3020−3023.
(8) (a) Mathias, L. J. Esterification and Alkylation Reactions
Employing Isoureas. Synthesis 1979, 1979, 561−576. (b) Biftu, T.;
Acton, J. J.; Berger, G. D.; Bergstrom, J. D.; Dufresne, C.; Kurtz, M.
M.; Marquis, R. W.; Parsons, W. H.; Rew, D. R.; Wilson, K. E.
Selective Protection and Relative Importance of the Carboxylic Acid
Groups of Zaragozic Acid A for Squalene Synthase Inhibition. J. Med.
Chem. 1994, 37, 421−424. (c) Nicolaou, K. C.; Yue, E. W.; Naniwa,
Y.; Dericcardis, F.; Nadin, A.; Leresche, J. E.; Lagreca, S.; Yang, Z.
Zaragozic acid A/Squalestatin S1: Synthetic and Retrosynthetic
Studies. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184−2187. (d) Hugger,
U.; Sharpless, K. B. Asymmetric Dihydroxylation Affords Enantiomeri-
cally Pure C12 Building Blocks from Traps, Traps,Cis-1,5,9-Cyclo-
dodecatriene. Tetrahedron Lett. 1995, 36, 6603−6606. (e) Crosignani,
S.; White, P. D.; Linclau, B. Microwave-Accelerated O-Alkylation of
Carboxylic Acids with O-Alkylisoureas. Org. Lett. 2002, 4, 2961−2963.
(f) Chighine, A.; Crosignani, S.; Arnal, M.-C.; Bradley, M.; Linclau, B.
Microwave-Assisted Ester Formation Using O-Alkylisoureas: A
Convenient Method for the Synthesis of Esters with Inversion of
Configuration. J. Org. Chem. 2009, 74, 4753−4762.
(12) Kuisle, O.; Quinoa, E.; Riguera, R. A General Methodology for
Automated Solid Phase Synthesis of Depsides and Depsipeptides.
Preperation of a Valinomycin Analogue. J. Org. Chem. 1999, 64, 8063−
8075.
(13) Thalluri, K.; Manne, S. R.; Dev, D.; Mandal, B. Ethyl 2-Cyano-2-
(4-nitrophenylsulfonyloxyimino)acetate-Mediated Lossen Rearrange-
ment: Single-Pot Racemization-Free Synthesis of Hydroxamic Acids
and Ureas from Carboxylic Acids. J. Org. Chem. 2014, 79, 3765−3775.
(14) Chakraborti, A. K.; Singh, B.; Chankeshwara, S. V.; Patel, A. R.
Protic Acid Immobilized on Solid Support as an Extremely Efficient
Recyclable Catalyst System for a Direct and Atom Economical
Esterification of Carboxylic Acids with Alcohols. J. Org. Chem. 2009,
74, 5967−5974.
(15) Manabe, K.; Iimura, S.; Sun, X.-M.; Kobayashi, S. Dehydration
Reactions in Water. Brønsted Acid−Surfactant-Combined Catalyst for
Ester, Ether, Thioether, and Dithioacetal Formation in Water. J. Am.
Chem. Soc. 2002, 124, 11971−11978.
(16) Morcillo, S. P.; Alvarez de Cienfuegos, L.; Mota, A. J.; Justicia, J.;
Robles, R. Mild Method for the Selective Esterification of Carboxylic
Acids Based on the Garegg−Samuelsson Reaction. J. Org. Chem. 2011,
76, 2277−2281.
(17) Garegg, P. J.; Samuelsson, B. Novel Reagent System for
Converting a Hydroxy-group into an Iodo-Group in Carbohydrates
with Inversion of Configuration. J. Chem. Soc., Chem. Commun. 1979,
978−980.
(18) Mamidi, N.; Manna, D. Zn(OTf)2-Promoted Chemoselective
Esterification of Hydroxyl Group Bearing Carboxylic Acids. J. Org.
Chem. 2013, 78, 2386−2396.
(19) (a) Rokhum, L.; Bez, G. A Practical One-pot Synthesis of Azides
Directly from Alcohols. J. Chem. Sci. 2012, 124, 687−691. (b) Rokhum,
L.; Bez, G. Ethyl Acrylate Conjugated Polystyryl-diphenylphosphine -
An Extremely Efficient Catalyst for Henry Reaction under Solvent-free
Conditions (SolFC). Can. J. Chem. 2013, 91, 300−306. (c) Rokhum,
L.; Bez, G. One-pot Solid Phase Synthesis of (E)-Nitroalkenes.
Tetrahedron Lett. 2013, 54, 5500−5504.
(20) Caputo, R.; Ferreri, C.; Noviello, S.; Palumbo, G. Use of
Polymeric Phosphine-Halogen Complexes in the Conversion of
Epoxides to Halohydrins. Synthesis 1986, 1986, 499−501.
(21) (a) Ogawa, H.; Amano, M.; Chihara, T. Facile and Highly
Selective Monoacylation of Symmetric Diols Adsorbed on Silica Gel
with Acetyl Chloride. Chem. Commun. 1998, 495−496. (b) Henrick,
C. A. The Synthesis of Insect Sex Pheromones. Tetrahedron 1977, 33,
1845−1889. (c) Babler, J. H.; Coghlan, M. J. A Facile Method for
Monoacetylation of Symmetrical Diols: Application to the Total
Synthesis of Z-8-Dodecenyl Acetate, the Sex Attractant of the Oriental
Fruit Moth. Tetrahedron Lett. 1979, 20, 1971−1974.
(22) Sharghi, H.; Sarvari, M. H. Al2O3/MeSO3H (AMA) As a New
Reagent with High Selective Ability for Monoesterification of Diols.
Tetrahedron 2003, 59, 3627−3633.
(23) (a) Aubin, Y.; Audran, G.; Vanthuyne, N.; Monti, H.
Chemoenzymatic Synthesis of Novel Adenosine Carbanucleoside
Analogues containing a Locked 3′-Methyl-2′, 3′ -β-Oxirane-Fused
System. Tetrahedron 2007, 63, 5050−5055. (b) Ghanem, A.; Aboul-
Enein, H. Y. Application of Lipases in Kinetic Resolution of
Racemates. Chirality 2005, 17, 1−15. (c) Schoffers, E.; Golebiowski,
A.; Johnson, C. R. Enantioselective Synthesis through Enzymatic
Asymmetrization. Tetrahedron 1996, 52, 3769−3826. (d) García-
Urdiales, E.; Alfonso, I.; Gotor, V. Enantioselective Enzymatic
Desymmetrizations in Organic Synthesis. Chem. Rev. 2005, 105,
313−354. (e) Ishizuka, Y.; Fujimori, H.; Noguchi, T.; Kawasaki, M.;
Kishida, M.; Nagai, T.; Imai, N.; Kirihara, M. Asymmetric Syntheses of
Pharmaceuticals Containing a Cyclopropane Moiety Using Catalytic
Asymmetric Simmons-Smith Reactions of Allylalcohols: Syntheses of
Optically Active Tranylcypromine and Milnacipran. Chem. Lett. 2013,
42, 1311−1313.
(9) (a) Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K.
V. P. P. Mitsunobu and Related Reactions: Advances and Application.
Chem. Rev. 2009, 109, 2551−2651. (b) Mitsunobu, O.; Yamada, M.
Preparation of Esters of Carboxylic and Phosphoric Acid via
Quaternary Phosphonium Salts. Bull. Chem. Soc. Jpn. 1967, 40,
2380−2382. (c) Ahn, C.; Correia, R.; DeShong, P. Mechanistic Study
of the Mitsunobu Reaction. J. Org. Chem. 2002, 67, 1751−1753.
(d) Ahn, C.; DeShong, P. An Approach to the Stereoselective
Synthesis of syn- and anti-1,3-Diol Derivatives. Retention of
Configuration in the Mitsunobu Reaction. J. Org. Chem. 2002, 67,
1754−1759.
(10) But, T. Y. S.; Toy, P. H. Organocatalytic Mitsunobu Reactions. J.
Am. Chem. Soc. 2006, 128, 9636−9637.
(11) (a) Wang, Y.; Zhang, F.; Zhang, Y.; Liu, J. O.; Ma, D. Synthesis
and Antitumor Activity of Cyclodepsipeptide Zygosporamide and its
Analogues. Bioorg. Bioorg. Med. Chem. Lett. 2008, 18, 4385−4387.
(b) Dhimitruka, I.; SantaLucia. Investigation of the Yamaguchi
Esterification Mechanism. Synthesis of a Lux-S Enzyme Inhibitor
Using an Improved Esterification Method. Org. Lett. 2006, 8, 47−50.
́
(24) (a) Framis, V.; Camps, F.; Clapes, P. Lipase-catalysed selective
monoacylation of 1,n-diols with vinyl acetate. Tetrahedron Lett. 2004,
45, 5031−5033. (b) Hamberg, A.; Magnusson, M. O.; Hu, F. J.; Hult,
D
ACS Comb. Sci. XXXX, XXX, XXX−XXX