1990
DOI: 10.1016/s0957-4166(00)82278-8
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The direct synthesis of the cyclic sulphamidate of (S)-prolinol: SimultaneousN-protection and activation towards nucleophilic displacement of oxygen.

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Cited by 65 publications
(25 citation statements)
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“…Tetrahydrofuran was distilled from sodium benzophenone ketyl and pyridine was distilled from calcium hydride. The following were prepared according to published procedures: 3-Methoxybut-1-yne (1i), [27] 4-(trimethylsilyloxy)pent-1-yne (1j), [28] 4-(tert-butyldimethylsilyloxy)pent-1-yne (1k), [29] 5-[tert-butyl(dimethyl)silyloxy]pent-1-yne (1l), [30] 4-pentynyl benzyl sulfide (1m), [26b] diethyl 6-bromo-6-hepten-1-yne-4,4-dicarboxylate (1o), [31] 6-cyclopropylidenehex-1-yne (1p), [32] 1-(trimethylsilyl)hepta-1,6-diyne (1q), [32] 2-[(E)-ethoxy]-1-ethynylcyclopropane (1y), [33] 1-hexen-5-yne (1z), [33] hexylphenylethyne (1he), [34] cyclopropylphenylethyne (1hc), [34] ethyl p-phenylethynylbenzoate (1hh 1 ), [35] methyl 4-(4-methoxyphenylethynyl)benzoate (1h 2 h 3 ), [35] bis(p-trifluoromethylphenyl)ethyne (1h 4 h 4 ), [35] 1,4-bis(p-trifluoromethylphenyl)-1,3-butadiyne (1h 4 z), [36] 1,4-bis(pmethoxyphenyl)-1,3-butadiyne (1h 3 z 2 ), [36] (2S)-methoxymethyl-pyrrolidine (2e), [37] methyl (2S)-pyrrolidinecarboxylate (2f), [38] diethyl (2S)-NЈ,NЈ-diethylpyrrolidinecarboxamide (2g), [39] (2R,5R)-dimethylpyrrolidine (2h), [40] trans-2,3-dimethylaziridine (2i), [41] (1S)-(1-phenyl)ethylmethylamine (2j), [42] pentacarbonyl[(2E)-3-(dimethylamino)-1-ethoxy-3-(trimethylsilyl)-2-propen-1-ylidene]chromium (3ga), [8] pentacarbonyl(1-ethoxy-2-hexyn-1-ylidene)chromium (5, R 1 ϭ nPr) [43] .…”
Section: Methodsmentioning
confidence: 99%
“…Tetrahydrofuran was distilled from sodium benzophenone ketyl and pyridine was distilled from calcium hydride. The following were prepared according to published procedures: 3-Methoxybut-1-yne (1i), [27] 4-(trimethylsilyloxy)pent-1-yne (1j), [28] 4-(tert-butyldimethylsilyloxy)pent-1-yne (1k), [29] 5-[tert-butyl(dimethyl)silyloxy]pent-1-yne (1l), [30] 4-pentynyl benzyl sulfide (1m), [26b] diethyl 6-bromo-6-hepten-1-yne-4,4-dicarboxylate (1o), [31] 6-cyclopropylidenehex-1-yne (1p), [32] 1-(trimethylsilyl)hepta-1,6-diyne (1q), [32] 2-[(E)-ethoxy]-1-ethynylcyclopropane (1y), [33] 1-hexen-5-yne (1z), [33] hexylphenylethyne (1he), [34] cyclopropylphenylethyne (1hc), [34] ethyl p-phenylethynylbenzoate (1hh 1 ), [35] methyl 4-(4-methoxyphenylethynyl)benzoate (1h 2 h 3 ), [35] bis(p-trifluoromethylphenyl)ethyne (1h 4 h 4 ), [35] 1,4-bis(p-trifluoromethylphenyl)-1,3-butadiyne (1h 4 z), [36] 1,4-bis(pmethoxyphenyl)-1,3-butadiyne (1h 3 z 2 ), [36] (2S)-methoxymethyl-pyrrolidine (2e), [37] methyl (2S)-pyrrolidinecarboxylate (2f), [38] diethyl (2S)-NЈ,NЈ-diethylpyrrolidinecarboxamide (2g), [39] (2R,5R)-dimethylpyrrolidine (2h), [40] trans-2,3-dimethylaziridine (2i), [41] (1S)-(1-phenyl)ethylmethylamine (2j), [42] pentacarbonyl[(2E)-3-(dimethylamino)-1-ethoxy-3-(trimethylsilyl)-2-propen-1-ylidene]chromium (3ga), [8] pentacarbonyl(1-ethoxy-2-hexyn-1-ylidene)chromium (5, R 1 ϭ nPr) [43] .…”
Section: Methodsmentioning
confidence: 99%
“…The crude product (1.5 g) was purified by column chromatography (silica gel, 3:1 hexane/EtOAc) followed by recrystallization (6a) was prepared according to the procedure of Harwood. 13 To a solution of (1R,2S)-1-amino-2-indanol (>99% ee, purchased from Aldrich, 100 mg, 0.67 mmol) and Et 3 N (102 mg, 1.0 mmol) in CH 2 Cl 2 (3 mL) was added SO 2 Cl 2 (136 mg, 1.0 mmol) at 0 °C. After stirring at this temperature for 1 h, the reaction mixture was poured into cold water (10 mL), and the whole was extracted with EtOAc (3 × 10 mL).…”
Section: -Phenylpropyl Sulfamate (5c)mentioning
confidence: 99%
“…The synthesis of 35 started from the readily available chiral (S)-alaninol which was N-Boc-protected (33), cyclized to the 2oxo-[1,2,3]oxathiazolidine 34 with thionylchloride and oxidised with NaIO 4 in the presence of catalytic amounts of RuO 2 to give the stable crystalline alkylating agent 35 [22]. Although described for the sulfate analogs and for the prolinol derived sulfamidate, the direct synthesis of the cyclic sulfamidate from (S)-prolinol using sulfuryl chloride did not work, presumably due to high reactivity of the N-Boc sulfamidate, which does not tolerate the presence of a nucleophilic base such as imidazole or pyridine [23] [24]. This powerful alkylating agent 35 was reacted with the lithio-indole derived from 36, in good yields and with complete retention of configuration (Scheme 5).…”
Section: (S)-aminopropyl Side Chain Incorporationmentioning
confidence: 99%