Two-carbon elongation/annulation of alcohols to nitriles

Lai, Jing Yu; Yu, Jurong; Hawkins, R. David; Falck, John R.

doi:10.1016/0040-4039(95)01125-2

Cited by 19 publications

(2 citation statements)

References 14 publications

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“…Improved Mitsunobu type reaction of 6 with phenylsulfonylacetonitrile and cyanomethylenetributylphoshorane in toluene at 100 °C stereospecifically afforded cis-4-substituted proline derivative 7 . Removal of the phenylsulfonyl group of 7 gave nitrile 8 . Reduction of 8 followed by guanylation gave guanidine 9 .…”

Section: Resultsmentioning

confidence: 99%

Restriction of a Peptide Turn Conformation and Conformational Analysis of Guanidino Group Using Arginine-Proline Fused Amino Acids: Application to Mini Atrial Natriuretic Peptide on Binding to the Receptor

et al. 2003

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Compounds (2S,4S)- and (2S,4R)-4-(2'-guanidinoethyl)proline have been synthesized as a conformationally restricted arginine. Their backbones fit the i + 1 position in a turn, and the side chains are restricted compared to that of arginine. These analogues were incorporated into mini atrial natriuretic polypeptide, which has an important turnlike conformation at Gly(6)-Arg(7)()-Met(8)-Asp(9). Structural analysis revealed that the size of the conformational space of Arg(7) on binding to the receptor was approximately one-third of the entire conformational space.

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Section: Resultsmentioning

confidence: 99%

Restriction of a Peptide Turn Conformation and Conformational Analysis of Guanidino Group Using Arginine-Proline Fused Amino Acids: Application to Mini Atrial Natriuretic Peptide on Binding to the Receptor

et al. 2003

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“…It is important to note that the desired N-alkylated product 7 was obtained in 59% yield from N-benzyltrifluoroacetamide (pK a 13.6), which had not successfully been used under the conditions of Mitsunobu reaction using Ph 3 P-DEAD. 16) In order to further confirm the efficiency of DBBQ, carbon-carbon bond forming reactions were next examined by using an active methylene compound such as (phenylsulfonyl)acetonitrile with a pK a value of 12.0 in DMSO 17) (Table IV). The DBBQ-mediated condensation of primary or secondary alkyl diphenylphosphinite with (phenylsulfonyl)acetonitrile proceeded smoothly at room temperature to form the corresponding mono-alkylated products 8c-8e in good to high yields (Entries 4-12) while the use of reactive benzyl diphenylphosphinite 1a afforded mono-and di-benzylated products 8a and 8b in a high total yield (Entries 1-3).…”

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confidence: 99%