✦ LIBER ✦

Oxazaborolidine catalyzed enantioselective reductions of cyclic meso-imides

✍ Scribed by Romeo Romagnoli; Eric C. Roos; Henk Hiemstra; Marinus J. Moolenaar; W. Nico Speckamp; Bernard Kaptein; Hans E. Schoemaker

Book ID: 104216326
Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 344 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)79972-2

No coin nor oath required. For personal study only.

✦ Synopsis

Cyclic meso-imides such as the cyclic cis-3&disubstituted succinimides 1 farm an interesting and useful class of starting mater% in the field of asymmetric synthesis. A single, enantioselective transfoxmation, naw9y a reduction of one of the carbonyls, leads to a product with three contiguous stereocenters. F-the 5hydroxy-2-pyrmlidinones

(2), beiig the products of such reductions, have been shown to be versatile building blocks for fhe synthesis of various natural product~.~ In recent years several research groups, including ours, have been interested in obtaining these hydroxylactams in optically pure form. Different methods have been studied for the asymmetric reduction of meso-imides in order to obtain the desired compounds, including yeast reductions and reductions of nreso-imides bearing a chiral N-substituent.3

Very recently, an enantioselective reduction method by using optically active BINAL-H complexes has been qortezd4

📜 SIMILAR VOLUMES

ChemInform Abstract: Oxazaborolidine-Cat

ChemInform Abstract: Oxazaborolidine-Catalyzed Enantioselective Reduction of Cyclic meso- Imides.

✍ M. OSTENDORF; R. ROMAGNOLI; I. CABEZA PEREIRO; E. C. ROOS; M. J. MOOLENAAR; W. N 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

Oxazaborolidine-Catalyzed Enantioselective Reduction of Cyclic meso-Imides. -It is found that several meso-imides can be reduced with high enantioselectivity by means of the oxazaborolidine shown in the scheme and subsequent ethanolysis or acetylation. By conversion to a benzenesulfonyllactam, it is

Desymmetrization of meso -Cyclic Imides

Desymmetrization of meso -Cyclic Imides via Enantioselective Monohydrogenation

✍ Takebayashi, Satoshi; John, Jeremy M.; Bergens, Steven H. 📂 Article 📅 2010 🏛 American Chemical Society 🌐 English ⚖ 222 KB

Asymmetric synthesis of 3,4-dihydroxyglu

Asymmetric synthesis of 3,4-dihydroxyglutamic acids via enantioselective reduction of cyclic meso-imide

✍ Makoto Oba; Shinichi Koguchi; Kozaburo Nishiyama 📂 Article 📅 2004 🏛 Elsevier Science 🌐 French ⚖ 148 KB

Origins of the enantioselectivity observ

Origins of the enantioselectivity observed in oxazaborolidine-catalyzed reductions of ketones

✍ Jones, Deborah K.; Liotta, Dennis C.; Shinkai, Ichiro; Mathre, David J. 📂 Article 📅 1993 🏛 American Chemical Society 🌐 English ⚖ 267 KB

Synthesis of Ro 25-8210 via an enantiose

Synthesis of Ro 25-8210 via an enantioselective oxazaborolidine-catalyzed reduction

✍ Kenneth G. Hull; Mike Visnick; William Tautz; Allen Sheffron 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 552 KB

Prochiral ketones which contain nitrogen atoms have been reduced enantioselectively with chiral oxazaborolidines in the presence of excess borane. However, the pyridine system has been shown to be a poor substrate for this asymmetric reduction. For example, catalytic reduction of 2acetylpyridine wit

Asymmetric catalytic reduction of meso-i

Asymmetric catalytic reduction of meso-imides

✍ Jahyo Kang; Jun Won Lee; Joo In Kim; Chongsuh Pyun 📂 Article 📅 1995 🏛 Elsevier Science 🌐 French ⚖ 216 KB