✦ LIBER ✦

Enantioconvergent synthesis of (−)-(S)- and (+)-(R)-2-acetyl-3,6-dihydroxycyclohex-2-enone starting from rac-6-hydroxy-3-methoxycyclohex-2-enone

✍ Scribed by V.G. Zaitsev; A.L. Mikhal'chuk

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 129 KB
Volume: 13
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.1066

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The synthesis of enantiomerically pure (−)‐(S)‐ and (+)‐(R)‐2‐acyl‐3,6‐dihydroxycyclohex‐2‐enone starting from diastereomerically pure N‐tosyl‐(S)‐proline esters 3‐methoxy‐6‐hydroxycyclohex‐2‐enone 1 is presented. An enantioconvergent synthesis of either (−)‐(S)‐ and (+)‐(R)‐2‐acyl‐3,6‐dihydroxycyclohex‐2‐enone starting with the racemic α‐ketol 1 through a conversion of (∼1:1) mixture of diastereomeric esters into one diastereomer by a repeated crystallization, followed by dimethylaminopyridine‐catalyzed equilibration as key steps is described. Chirality 13:488–492, 2001. © 2001 Wiley‐Liss, Inc.

📜 SIMILAR VOLUMES

Synthesis of the rac-6-hydroxy-3-methoxy

Synthesis of the rac-6-hydroxy-3-methoxycyclohex-2-enone and resolution through recrystallization of its diastereomeric N-tosyl-(S)-proline esters

✍ V.G. Zaitsev; D.G. Sachava; G.S. Yankovskaya; N.I. Garbuz 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 116 KB

The synthesis and resolution of rac-6-hydroxy-3-methoxycyclohex-2-enone, by fractional crystallization of diastereomeric esters of N-protected (S)-proline was shown to be an effective method for preparation of both pure diastereomers (>95% d.e., according to (1)H NMR data). The absolute configuratio

Furylcyclohexenones. Part 3. Synthesis a

Furylcyclohexenones. Part 3. Synthesis and Properties of 6-Acetyl-3(5)-furylcyclohex-2-enones. Molecular and Crystal Structure of 6-Acetyl-3-(2-furyl)-5-phenylcyclohex-2-enone.

✍ E. B. Usova; L. I. Lysenko; V. E. Zavodnik; E. K. Yablonskaya; G. D. Krapivin 📂 Article 📅 2004 🏛 John Wiley and Sons ⚖ 87 KB 👁 1 views

ChemInform Abstract: Synthesis of Bipyra

ChemInform Abstract: Synthesis of Bipyrazoles and Pyrazoloisoxazoles from 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one.

✍ Abderrahman Bendaas; Maamar Hamdi; Nicole Sellier 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 1 views

ChemInform Abstract: C45- and C50-Carote

ChemInform Abstract: C45- and C50-Carotenoids. Part 7. Total Synthesis of (all-E,2R,6R,2′R,6′R)- and (all-E,2R,6S,2′R,6′S)-2,2′-Bis (4-hydroxy-3-methylbut-2-enyl)-γ,γ-carotene (Sarcinaxanthin).

✍ M. LANZ; B. BARTELS; H. PFANDER 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

ChemInform Abstract: Synthesis of (1R,2S

ChemInform Abstract: Synthesis of (1R,2S,3S,4R,5R,7S)-2,3,4-Tris-(phenylmethoxy)-6,8-dioxabicyclo (3.2.1)octan-7-ol from 1R,2R,3S-Tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene by Ozonolysis.

✍ Hari Babu Mereyala; Bhavani Chadalawada; Sreenivasulu Guntha 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

ChemInform Abstract: Syn-Selective Micha

ChemInform Abstract: Syn-Selective Michael Addition of Amines to Bis-enones: Synthesis of 1, 3,4,7-Tetrasubstituted (4R,5S,6S,7R)-Hexahydro-5,6-dihydroxy-2H-1,3- diazepin-2-ones.

✍ E. P. SCHREINER; A. PRUCKNER 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 1 views

Syn-Selective Michael Addition of Amines to Bis-enones: Synthesis of 1, 3,4,7-Tetrasubstituted (4R,5S,6S,7R)-Hexahydro-5,6-dihydroxy-2H-1,3-diazepin-2-ones. -The O-protected title compounds (IX), seven-membered cyclic ureas, are useful as intermediates in the synthesis of HIV-proteinase inhibitors.