Catalytic asymmetric synthesis of a functionalized indolizidine derivative. A useful intermediate suitable for the synthesis of various glycosidase inhibitors
Indolizidine derivative 7 has been sythesized in up 86% ee by an asymmetric Heack reaction (Pd(O)-BPPFOH, Ag-exchanged zeolite) starting with prochiral alkenyl iodide 5. Conversion of 7 to δconiceine (9) is also described.
Asymmetrie synthesis of unsaturated monocyclic and bicyclic nitrogen heterocycles
Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R) CHCH2 and allylatlon, or acylatlon with but-3-enoic acid, followed by ring-closing metathesis resulted In the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anlsomycln (R = p-MeOC 6H4). Extension of this methodology with R = CH 2CHCH2 employing two ring-closing metatheses resulted In the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.
Nomura, Hiroshi,Richards, Christopher J.
supporting information; experimental part
p. 2892 - 2895
(2009/12/06)
Asymmetric Heck reaction of alkenyl iodides in the presence of silver salts. Catalytic asymmetric synthesis of decalin and functionalized indolizidine derivatives
Decalin derivatives 3 (up to 80% ee) and indolizidine derivative 6 (up to 86% ee) have been synthesized by an asymmetric Heck reaction starting with prochiral alkenyl iodides 1 and 4, respectively. The important role of silver salts in the asymmetric Heck
Sato,Nukui,Sodeoka,Shibasaki
p. 371 - 382
(2007/10/02)
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