Stereospecific synthesis of α-lipoic acid

Menon, Rani B.; Kumar, Manjeet; Ravindranathan, T.

doi:10.1016/s0040-4039(00)96717-0

Cited by 23 publications

(4 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Treatment of aldol product 6a afforded the 1,3‐diol 8 in 61% yield. The conversion of the methyl ester analogue of 8 into ( R )‐α‐lipoic acid ( 1 ) has already been reported 20. A short and enantioselective formal total synthesis of ( R )‐ 1 with an asymmetric aldol reaction as a crucial step has thus been established as shown in Equation (1 ). …”

Section: Resultsmentioning

confidence: 97%

Optimisation, Scope and Limitations of Enantioselective Aldol Reactions of an S-Ketene Silyl Acetal with Aliphatic Aldehydes under (R)-BINOL-Titanium(IV) Catalysis Conditions

et al. 2002

View full text Add to dashboard Cite

The Mukaiyama aldol reaction between the functionalised aldehydes 5 and the S‐ketene silyl acetal 2 catalysed by 1,1′‐binaphthyl‐derived chiral titanium(IV) complex 4 afforded the corresponding aldol products 6 in good yields and with good to excellent enantioselectivities. The chemical yield could further be enhanced, without loss of stereoselection, by addition of phenol and/or molecular sieves. The presented aldol reactions with aluminium, boron and ytterbium‐BINOL catalysts demonstrate that only low chiral induction can be achieved. Aldol product 6a was converted into an α‐lipoic acid precursor 8, thus providing a formal synthesis of this biologically active compound. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

show abstract

Section: Resultsmentioning

confidence: 97%

Optimisation, Scope and Limitations of Enantioselective Aldol Reactions of an S-Ketene Silyl Acetal with Aliphatic Aldehydes under (R)-BINOL-Titanium(IV) Catalysis Conditions

et al. 2002

View full text Add to dashboard Cite

show abstract

“…In 1987, a short and highly stereospecific synthesis of S -ALA using menthone as a recyclable chiral auxiliary was presented by Menon et al ( Scheme 33 ). 45 Dithiane 145, the starting material, served as the chiral template that controlled the regiochemistry of the subsequent oxidation to provide 146 as a single regioisomer in 80% yield. The stereoselective alkylation of 146 with 5-bromovaleric acid 147 in the presence of lithium diisopropylamide as a base in THF resulted in the carboxylic acid derivative 148, which was hydrolyzed in aqueous HCl to yield S -ALA.…”

Section: Synthesis Of R -Alamentioning

confidence: 99%

α-Lipoic acid chemistry: the past 70 years

Wang,

Ling,

Wang

et al. 2023

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…23 Still lipoic acid remains a favorite molecule as seen in recent publications. [12][13][14][15][16][17][18][19][20][21][22][23] Previous syntheses of lipoic acid involve either complex routes, complex intermediates, or harsh reaction conditions.…”

Section: Figurementioning

confidence: 99%