The Pummerer-type reaction mediated ring-opening of 2-alkyl substituted 1-[(2-methoxyethoxy)methoxy]-2-(phenylsulfinyl)cyclopropanes

Authors
Pohmakotr, M Moosophon, P Pisutjaroenpong, S Tuchinda, P Reutrakul, V
Citation
M. Pohmakotr et al., The Pummerer-type reaction mediated ring-opening of 2-alkyl substituted 1-[(2-methoxyethoxy)methoxy]-2-(phenylsulfinyl)cyclopropanes, TETRAHEDR L, 42(26), 2001, pp. 4389-4391
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
26
Year of publication
2001
Pages
4389 - 4391
Database
ISI
SICI code
0040-4039(20010625)42:26<4389:TPRMRO>2.0.ZU;2-I
Abstract
alpha -Lithiated 1-[(2-methoxyethoxy)methoxy]-2-(phenylsylfinyl)cyclopropan e reacted smoothly with alkylating agents to afford the corresponding alpha -alkylated cyclopropylsulfoxides, which underwent the Pummerer-type reacti on mediated ring-opening at low temperature (-78 degreesC) by employing TFA A/(Pr2NEt)-N-i/CH2Cl2 to give mixtures of beta-(phenylthio)-alpha,beta- and gamma,delta -unsaturated aldehydes. (C) 2001 Elsevier Science Ltd. All rig hts reserved.