Catalytic and Highly Enantioselective Reactions of α‐Sulfonyl Carbanions with Chiral Bis(oxazoline)s | Zendy

Nakamura Shuichi | Zendy; Hirata Norimune | Zendy; Yamada Ryusuke | Zendy; Kita Takeshi | Zendy; Shibata Norio | Zendy; Toru Takeshi | Zendy

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Catalytic and Highly Enantioselective Reactions of α‐Sulfonyl Carbanions with Chiral Bis(oxazoline)s

Author(s) -

Nakamura Shuichi,

Hirata Norimune,

Yamada Ryusuke,

Kita Takeshi,

Shibata Norio,

Toru Takeshi

Publication year - 2008

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200800221

Subject(s) - enantioselective synthesis , oxazoline , carbanion , sulfonyl , chemistry , catalysis , enantiomer , enantiomeric excess , trifluoromethyl , stoichiometry , organic chemistry , sulfone , alkyl

The enantioselective reactions of lithiated benzyl trifluoromethyl sulfones with a substoichiometric amount of a bis(oxazoline) and various aldehydes is disclosed. The products were formed with excellent diastereo‐ and enantioselectivities. Fluorination of the sulfone with N ‐fluorobenzenesulfonimide and a stoichiometric amount of a bis(oxazoline) gave products with extremely high enantioselectivities (up to 99 % ee ; ee =enantiomeric excess). The enantioselective reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway.

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