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One-Pot Diastereoselective Synthesis of Densely Functionalized 2H-Indeno[2,1-b]furans. Single-Crystal X-Ray Structure of Dimethyl 8,8a-Dihydro-8-oxo-8a-(2,2,2-trichloroethoxy)-2H-indeno[2,1-b]furan-2,3-di­carboxylate

✍ Scribed by Ali Ramazani; Nader Noshiranzadeh; Alieh Ghamkhari; Katarzyna Ślepokura; Tadeusz Lis

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
250 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Highly reactive 1 : 1 intermediates were produced in the reaction of Ph~3~P and dialkyl acetylenedicarboxylates (=dialkyl but‐2‐ynedioates). Protonation of these intermediates by alcohols (2,2,2‐trichloroethanol, propargyl alcohol (=prop‐2‐yn‐1‐ol), MeOH, benzyl alcohol, and allyl alcohol (=prop‐2‐en‐1‐ol) led to vinyltriphenylphosphonium salts 4, which underwent a Michael addition reaction with the conjugate base to produce the corresponding stabilized phosphonium ylides 5 (Scheme). Wittig reaction of the stabilized phosphonium ylides with ninhydrin (6) led to the corresponding densely functionalized 2__H__‐indeno[2,1‐b]furans 10 in fairly good yields (Table 1). The structures of the final products were confirmed by IR, ^1^H‐ and ^13^C‐NMR spectroscopy, and mass spectrometry. The configuration of dimethyl 8,8a‐dihydro‐8‐oxo‐8a‐(2,2,2‐trichloroethoxy)‐2__H__‐indeno[2,1‐b]furan‐2,3‐dicarboxylate (10a) was established by a single‐crystal X‐ray structure determination, establishing that the one‐pot multicomponent condensation reaction was completely diastereoselective.

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