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Synlett

Volumn , Issue 16, 2008, Pages 2455-2458

Preparation and some synthetic applications of 2-hydroxyethyl-substituted cyclopropylamines

(4) Joosten, Antoine a Vasse, Jean Luc a Bertus, Philippe a,b Szymoniak, Jan a

a CNRS (France)

b UNIVERSITÉ DU MAINE (France)

Author keywords

Amino acids; Cyclopropanes; Nitriles; Titanium; Transition metals

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOPROPANE DERIVATIVE; GLUTAMIC ACID DERIVATIVE; HYDROXYL GROUP; NITRILE; PROPYLAMINE; PYRROLIZIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; CYCLOPROPANATION; DIASTEREOISOMER; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 54249100087 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078180 Document Type: Article

Times cited : (13)

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- Selected Data of 1-[2-Hydroxy-2-(2-methoxyphenyl)-ethyl]-4-azaspiro[2. 4]heptan-5-one (6f) Minor diastereomer: 1H NMR (250 MHz, MeOD, δ, 0.49 (t, J, 6.0 Hz, 1 H, 0.76 (dd, J, 9.6, 6.0 Hz, 1 H, 1.00 (ddd, J, 9.5, 6.6, 4.4 Hz, 1 H, 1.62 (ddd, J, 14.0, 9.5, 5.8 Hz, 1 H, 1.81-1.85 (m, 1 H, 1.93 (ddd, J, 14.0, 7.6, 4.4 Hz, 1 H, 2.15-2.24 (m, 3 H, 3.84 (s, 3 H, 5.04 (dd, J, 7.6, 5.8 Hz, 1 H, 6.88-6.96 (m, 2 H, 7.21 (td, J, 7.5, 1.4 Hz, 1 H, 7.38 (dd, J, 7.5, 1.4 Hz, 1 H, 13C NMR (62.9 MHz, MeOD, δ, 15.5, 21.4, 31.5, 31.7, 38.0, 44.7, 55.8, 69.7, 111.3, 121.5, 127.6, 129.2, 133.9, 157.6, 180.4. IR (KBr, 3420, 2523, 2076, 1651, 1457, 1117 cm-1. Major diastereomer: 1H NMR (250 MHz, MeOD, δ, 0.41 (t, J, 6 Hz, 1 H, 0.70 (dd, J, 9.5, 6.0 Hz, 1 H, 0.89-0.95 (m, 1 H, 1.64-1.68 (m, 1 H, 1.83 ddd, J, 14.3, 8.8, 5.5 Hz, 1 H
- +: 192.1443; found: 192.1442.

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43
- 33847793194
- The pyrrolizidine analogue 7 was recently obtained by Ti-mediated cyclopropanation of unsaturated imides, see: Bertus, P.; Szymoniak, J. Org. Lett. 2007, 9, 659.
- The pyrrolizidine analogue 7 was recently obtained by Ti-mediated cyclopropanation of unsaturated imides, see: Bertus, P.; Szymoniak, J. Org. Lett. 2007, 9, 659.

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