✦ LIBER ✦

Asymmetric synthesis of 5-(1-hydroxyalkyl)-5-methyl-5H-furan-2-ones

✍ Scribed by Hélène Bruyère; Stéphanie Ballereau; Mohamed Selkti; Jacques Royer

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 257 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)00937-2

No coin nor oath required. For personal study only.

✦ Synopsis

The reactivity of 5-methyl-4-(pyrrolidin-1-yl)-5H-furan-2-one with aldehydes and with acyl chlorides followed by reduction was studied. The aldol condensation gave predominantly the anti aldol product when the acylation -reduction sequence led exclusively to the syn product. The use of a chiral pyrrolidine, (S)-2-methoxymethylpyrrolidine (SMP), allowed the synthesis of enantio-enriched compounds, the acylation -reduction leading to the (R,R) addition product.

📜 SIMILAR VOLUMES

Synthesis of new homochiral polyfunction

Synthesis of new homochiral polyfunctionalized furan-2(5H)-ones

✍ M. Rosario Martín; Ana I. Mateo 📂 Article 📅 1994 🏛 Elsevier Science 🌐 English ⚖ 526 KB

## Abatractr The synthesis of enantio-and diastereomerically pure (55)4bromo-5(Imenthyloxy)furan2(5H)-one (2) and a general method to obtain (5s)4alkylarnino-and 4alkylthio-5-(l-menthyloxy)furan-2(5H)-ons in very good yields are described. 5-Alkoxyfuran-2(5H)-ones are useful intermediates in organ

ChemInform Abstract: Stereoselective Syn

ChemInform Abstract: Stereoselective Syntheses of syn 5-[1-Hydroxy-2-(2-bromo-phenyl)-ethyl]-5-methyl-5H-furan-2-one and syn 5-[1-Hydroxy-2-(2-methoxy-phenyl)-ethyl]-5-methyl-5H-furan-2-one.

✍ Elena Redero; Celso Sandoval; Francisco Bermejo 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 2 views

Synthesis of diastereoisomerically pure

Synthesis of diastereoisomerically pure 5-substituted 5-(l-menthyloxy)-4-(pyrrolidin-1-yl)furan-(5H)-ones

✍ M. Rosario Martín; Ana I. Mateo 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 573 KB

Reactions of lithium enolate 2, generated from (5S)-5-(l-menthyloxy)-4-(pyrrolidin-l-yl)furan-2(5H)-one (la) or from the mixture of epimers at C-5 (la, lb), with different sort of electrophiles, such as alkylating agents, aldehydes, acyl chlorides, dimethyl carbonate and a Michael acceptor, occur re

Recent Developments in the Synthesis of

Recent Developments in the Synthesis of Furan-2(5H)-ones

✍ Neil B. Carter; Adam E. Nadany; J. B. Sweeney 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 52 KB 👁 2 views

4,5-Dihydroxyimidazolidin-2-ones in α-ur

4,5-Dihydroxyimidazolidin-2-ones in α-ureidoalkylation ofN-carboxyalkyl-,N-hydroxyalkyl-, andN-aminoalkylureas 5. Synthesis ofN-hydroxyalkyl-1,5-diphenylglycolurils

✍ G. A. Gazieva; V. V. Baranov; A. N. Kravchenko 📂 Article 📅 2010 🏛 Springer 🌐 English ⚖ 193 KB

(RS,RS)-5-[Hydroxy(4-methylphenyl)methyl

(RS,RS)-5-[Hydroxy(4-methylphenyl)methyl]furan-2(5H)-one

✍ Ollevier, Thierry ;Bouchard, Jean-Emmanuel ;Desyroy, Valerie ;Tessier, Christian 📂 Article 📅 2007 🏛 International Union of Crystallography 🌐 English ⚖ 349 KB

The crystal structure of the racemic title compound, C~12~H~12~O~3~, allowed the determination of the relative configuration at the two stereogenic centers. For the __R,R__ isomer, the O—C—C—O and C—C—C—C torsion angles around the bond between the two methine C atoms are 62.38 (15) and −175.49 (13)°