Lewis acid catalyzed condensation between glycine iminoester enolates and p-tolylsulfinimines

Synlett

Volumn , Issue 10, 1999, Pages 1543-1546

  Viso, Alma ^a   Fernández De La Pradilla, Roberto ^b   García, Ana ^b   Alonso, Marta ^b   Guerrero Strachan, Carlos ^b   Fonseca, Isabel ^c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

Amino alcohols; Asymmetric synthesis; Chiral auxiliaries; Sulfinimines; Vicinal diamines

Indexed keywords

SULFINIC ACID DERIVATIVE; TOLYLSULFINIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; POLYMERIZATION; SPAIN; STEREOCHEMISTRY; SYNTHESIS;

EID: 0345425817     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2898     Document Type: Article

References (58)

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46. 2 efficiently promoted the desired cyclization.
47. In most cases, small amounts (5-10%) of N-sulfinyl-diaminoesters produced by hydrolysis of iminoester intermediates 3, were isolated.
48. 1H NMR at intervals of about 24 h. In most cases, after 4-6 days we could not detect significant changes in the composition of the mixture. This behavior demonstrates that a stepwise reaction pathway is operative for these processes. At this stage, we do not have a clear understanding of the rationale behind the failure of these glycine derived dipoles to engage in uncatalyzed 1,3-dipolar cycloadditions with sulfinimines.
49. 1H NMR (300 MHz) δ 2.28 (s, 3 H), 3.76 (s, 3 H), 4.01 (d, 1 H, J = 7.2 Hz), 5.07 (d, 1 H, J = 7.2 Hz), 5.93 (s, 1 H).
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53. In some experiments, particularly at short reaction times, variable mixtures of 9 and 12 were obtained.
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55. 2O gave a 50:50 mixture of 9 and a diastereomer (structure not shown). Desulfinylation of this mixture afforded exclusively racemic diaminoalcohol 11.
56. 1H NMR (200 MHz) δ 1.60 (br s, 1 H), 2.25 (s, 3 H), 2.88 (ddd, 1 H, J = 8.8, 5.3, 3.5 Hz), 3.36 (d, 1 H, J = 13.3 Hz), 3.51 (d, 1 H, J. = 13.3 Hz), 3.56 (m, 2 H), 4.45 (dd, 1 H, J = 7.5, 3.5 Hz), 5.64 (d, 1 H, J = 7.5 Hz), 6.99-7.08 (m, 6 H), 7.13-7.25 (m, 6 H), 7.38 (d, 2 H, J = 8.3 Hz). The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
57. 4/LiI in a related context, see: Sudharshan, M.; Hultin, P. G. Synlett 1997, 171-172.
58. 3 gave a 61:39 mixture of 4a and 4b.