From 1‐(Silyloxy)Butadiene to 4‐Amino‐4‐Deoxy‐ DL ‐Erythrose and to 1‐Amino‐1‐Deoxy‐ DL ‐Erythritol Derivatives  via  Hetero‐ Diels ‐ Alder  Reactions with Acylnitroso Dienophiles | Zendy

Defoin Albert | Zendy; Pires Joaquim | Zendy; Streith Jacques | Zendy

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From 1‐(Silyloxy)Butadiene to 4‐Amino‐4‐Deoxy‐ DL ‐Erythrose and to 1‐Amino‐1‐Deoxy‐ DL ‐Erythritol Derivatives via Hetero‐ Diels ‐ Alder Reactions with Acylnitroso Dienophiles

Author(s) -

Defoin Albert,

Pires Joaquim,

Streith Jacques

Publication year - 1991

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19910740806

Subject(s) - chemistry , erythritol , yield (engineering) , hydroxylation , stereochemistry , amino acid , cleavage (geology) , organic chemistry , biochemistry , materials science , metallurgy , enzyme , geotechnical engineering , fracture (geology) , engineering

Acylnitroso dienophiles 4 reacted instantly with 1‐(silyloxy)butadiene 5α and led in good yield to the regioisomeric cycloadducts 6 (major) and 7 (minor; Scheme 2, Table 1 ). cis ‐Hydroxylation of these primary cycloadducts with OsO 4 (catalyst) occurred stereospecifically and in high yield (→ 8 and 9 , resp.; Scheme 2 ). It was followed by reductive ring cleavage to give either 1‐amino‐1‐deoxy‐ DL ‐erythritol or 4‐amino‐4‐deoxy‐ DL ‐erythrose derivatives 10 and 14 , respectively, depending on the nature of the reducing agent ( Schemes 3 and 4 ).

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