Improvements in the Preparation of DL-Threonic and DL-Erythronic Acids

Glattfeld, J. W. E.; Rietz, Edward

doi:10.1021/ja01861a073

Cited by 18 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Racemic cis , vic ‐dihydroxylation/lactonization of the achiral β,γ‐unsaturated carboxylic acid 71 by Glattfeld and Rietz . Reagents and conditions : (a) OsO 4 (0.01 mol‐%), Ba(ClO 3 ) 2 (0.2‐fold molar amount), H 2 O, <35 °C, 1 d; once more OsO 4 (0.01 mol‐%), 2 d; 35 %.…”

Section: γ‐Lactone Syntheses By Dihydroxylation Of βγ‐Unsaturatedmentioning

confidence: 98%

“…Racemic cis,vic-dihydroxylation/lactonization of the achiral ,γunsaturated carboxylic acid 71 by Glattfeld and Rietz. [23] When the dihydroxylation of Scheme 13 was effected with OsO 4 rather than with KMnO 4 it delivered the previously mentioned lactone rac-70 in a 57:43 mixture (29 % yield) with its epimer rac-epi-70 (Scheme 15, bottom). [22] An OsO 4 -catalyzed cis,vic-dihydroxylation of the corresponding ,γ-unsaturated carboxylic acid rac-73 provided the same lactones as an 84:16 mixture in 84 % yield (Scheme 15, top).…”

Section: γ-Lactone Syntheses By Dihydroxylation Of γ-Unsaturated Carmentioning

confidence: 99%

“…The first racemic cis , vic ‐dihydroxylation of a β,γ‐unsaturated carboxylic acid, wihch led to a β‐hydroxy‐γ‐lactone, was reported in 1940 . It affected the achiral acid 71 of Scheme .…”

Section: γ‐Lactone Syntheses By Dihydroxylation Of βγ‐Unsaturatedmentioning

confidence: 99%

See 2 more Smart Citations

Nonracemic γ‐Lactones from the Sharpless Asymmetric Dihydroxylation of β,γ‐Unsaturated Carboxylic Esters

Neumeyer

Brückner

2016

Eur J Org Chem

View full text Add to dashboard Cite

Since Sharpless' discovery of the asymmetric dihydroxylation of C=C double bonds in the late 1980s this reaction has become a powerful tool of synthetic organic chemistry. As a consequence, this transformation has been reviewed repeatedly and extensively. The present microreview focuses on Sharpless' asymmetric dihydroxylations (from here on “SADs”) of β,γ‐unsaturated carboxylic esters. These SADs differ from most others in that they provide not nonracemic 1,2‐diols but follow‐up products thereof. Bearing ester groups at appropriate distances, the SAD‐based 1,2‐diols obtained from β,γ‐unsaturated carboxylic esters lactonize readily under SAD conditions. Accordingly, SADs of β,γ‐unsaturated carboxylic esters furnish nonracemic β‐hydroxy‐γ‐lactones in a single operation. We show that this SAD route represents a – or even the most – potent easy‐to‐handle route to nonracemic butanolides and butenolides “of almost all kinds”. The span covered is from pioneering racemic work to applications in natural product synthesis. Some non‐butanolide and non‐butenolide target syntheses are included, especially those of tetrahydrofurans.

show abstract

Section: γ‐Lactone Syntheses By Dihydroxylation Of βγ‐Unsaturatedmentioning

confidence: 98%

Section: γ-Lactone Syntheses By Dihydroxylation Of γ-Unsaturated Carmentioning

confidence: 99%

See 1 more Smart Citation

Nonracemic γ‐Lactones from the Sharpless Asymmetric Dihydroxylation of β,γ‐Unsaturated Carboxylic Esters

Neumeyer

Brückner

2016

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…The hypothesis that 2 would condense with an α-unsubstituted amine under conditions sufficiently mild to prevent a concomitant cyclisation was tested. The amines 5b 6 and 5c were prepared and found to condense with 2 simply on stirring in CHCl 3 at room temp. in the presence of NEt 3 .…”

mentioning

confidence: 99%

Preparation of imidazo[1,2-c]pyrimidinones from a chloropyrimidine and an electron poor ω-allylic amine

Heaney¹,

Bourke²,

Burke³

et al. 1998

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

Synthesis of the title ring system by a sequential intermolecular nucleophilic displacement and intramolecular 'conjugate' addition has been achieved both as a one pot and as a stepwise procedure; an X-ray structure determination has been carried out to distinguish between the possible isomeric structures 8c-I and 8c-II.The alkenylamidopyrimidines 1 were identified as key starting materials in an on-going project to prepare ring fused diazepines.

show abstract