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Highly efficient photochemical addition of tertiary amines to electron deficient alkenes. Diastereoselective addition to (5R)-5-menthyloxy-2[5H]-furanone

✍ Scribed by Samuel Bertrand; Cédric Glapski; Norbert Hoffmann; Jean-Pierre Pete

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
257 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Tertiary amines derived from pyrrolidines can be added veD' efficiently (isolated yields up to 94%) to (SR)-5-mentyloxy-2[5H]-furanone. The addition, which follows a radical chain mechanism initiated by a photoinitiated electron transfer (PET) from the tertiary amine to the excited aromatic ketone, occurs with a complete facial selectivity on the furanone ring. The method can be generalized to the addition of tertiary, amines and N-protected secondary amines to electron deficient alkenes.

📜 SIMILAR VOLUMES

Stereoselective radical addition of tert
Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone: Application to the enantioselective synthesis of (−)-isoretronecanol and (+)-laburnine
✍ Samuel Bertrand; Norbert Hoffmann; Jean-Pierre Pete 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 138 KB

The adducts of a stereoselective radical addition of tertiary amines with (5R)-5-menthyloxy-2[5H]-furanone were transformed very efficiently into enantiomerically pure pyrrolizidine and indolizidine alkaloids, through a three steps sequence.

ChemInform Abstract: Stereoselective Rad
ChemInform Abstract: Stereoselective Radical Addition of Tertiary Amines to (5R)-5-Menthyloxy-2[5H]-furanone: Application to the Enantioselective Synthesis of (-)-Isoretronecanol and (+)-Laburnine.
✍ Samuel Bertrand; Norbert Hoffmann; Jean-Pierre Pete 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 2 views

Application to the Enantioselective Synthesis of (-)-Isoretronecanol and (+)-Laburnine. -Compound (I) is an adduct of a stereoselective radical addition of a tertiary amine with (5R)-5-menthyloxy-2[5H]-furanone. It is readily transformed to (+)-laburnine (IV) in a three-step sequence. Similarly, (-