Asymmetric 1,6‐Induction in Hetero‐Diels–Alder Reactions of Chiral Oxabutadienes for a De Novo Synthesis of Enantiomerically Pure Carbohydrates: Lewis Acid Dependent Reversal of Facial Selectivity | Zendy

Tietze Lutz F. | Zendy; Schneider Christoph | Zendy; Montenbruck Andrea | Zendy

Premium

Asymmetric 1,6‐Induction in Hetero‐Diels–Alder Reactions of Chiral Oxabutadienes for a De Novo Synthesis of Enantiomerically Pure Carbohydrates: Lewis Acid Dependent Reversal of Facial Selectivity

Author(s) -

Tietze Lutz F.,

Schneider Christoph,

Montenbruck Andrea

Publication year - 1994

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199409801

Subject(s) - selectivity , lewis acids and bases , chemistry , asymmetric induction , enol ether , diels–alder reaction , chiral lewis acid , enol , ether , organic chemistry , enantioselective synthesis , stereochemistry , catalysis

Excellent endo/exo selectivity and very good induced diastereoselectivity are achieved by hetero‐Diels‐Alder reactions of oxabutadienes such as 1 , accessible from chiral oxazolidinones, with the enol ether 2 in the presence of Lewis acids. The facial selectivity can be reversed by varying the Lewis acid. The endo product is formed almost exclusively from 1 and 2 with Me 2 AlCl as promotor. In contrast, the other endo product 4 predominates with trimethylsilyltriflate (TMS‐OTf) as initiator.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research