Synthesis of optically active heterocyclic compounds via deracemization of 1, 2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of …

K Matsumoto, K Usuda, H Okabe, M Hashimoto…

Index: Matsumoto, Kazutsugu; Usuda, Kazumasa; Okabe, Hirokazu; Hashimoto, Manabu; Shimada, Yasutaka Tetrahedron Asymmetry, 2013 , vol. 24, # 2-3 p. 108 - 115

Full Text: HTML

Citation Number: 4

Abstract

We have succeeded in accomplishing the deracemization of (±)-2-acetoxydecyl and (±)- acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-γ-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl ...

Related Articles:

Synthesis of 10, 11-dihydroleukotriene B4 metabolites via a nickel-catalyzed coupling reaction of cis-bromides and trans-alkenyl borates

[Nakayama, Yuji; Kumar, G. Biju; Kobayashi, Yuichi Journal of Organic Chemistry, 2000 , vol. 65, # 3 p. 707 - 715]

C-1 Reactivity of 2, 3-epoxy alcohols via oxirane opening with metal halides: applications and synthesis of naturally occurring 2, 3-octanediol, muricatacin, 3-octanol, …

[Bonini, Carlo; Federici, Chiara; Rossi, Leucio; Righi, Giuliana Journal of Organic Chemistry, 1995 , vol. 60, # 15 p. 4803 - 4812]

Catalytic asymmetric preparation of polyfunctional protected 1, 2-diols and epoxides

[Eisenberg, Christina; Knochel, Paul Journal of Organic Chemistry, 1994 , vol. 59, # 14 p. 3760 - 3761]

Asymmetric halogenation of camphor-10-sulfonic acid derived esters: an efficient new route to enantiomerically pure halohydrins and epoxides.

[Oppolzer, Wolfgang; Dudfield, Philip Tetrahedron Letters, 1985 , vol. 26, # 41 p. 5037 - 5040]

C-1 Reactivity of 2, 3-epoxy alcohols via oxirane opening with metal halides: applications and synthesis of naturally occurring 2, 3-octanediol, muricatacin, 3-octanol, …

[Bonini, Carlo; Federici, Chiara; Rossi, Leucio; Righi, Giuliana Journal of Organic Chemistry, 1995 , vol. 60, # 15 p. 4803 - 4812]

More Articles...