Asymmetric Tandem Wittig Rearrangement/Mannich Reactions | Zendy

Giampietro Natalie C. | Zendy; Wolfe John P. | Zendy

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Asymmetric Tandem Wittig Rearrangement/Mannich Reactions

Author(s) -

Giampietro Natalie C.,

Wolfe John P.

Publication year - 2010

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201000609

Subject(s) - chemistry , stereoselectivity , wittig reaction , tandem , alcohol , cleavage (geology) , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , materials science , geotechnical engineering , fracture (geology) , engineering , composite material

The choice is yours : A highly stereoselective synthesis of α‐alkyl‐α‐hydroxy‐β‐amino esters is accomplished through a tandem Wittig‐rearrangement/Mannich reaction sequence. Transformations of N ‐benzyl or N ‐Boc imines proceed with high selectivity for formation of syn ‐amino alcohol derivatives, whereas N ‐Boc‐2‐(phenylsulfonyl)amines generate anti ‐amino alcohol products. Auxiliary cleavage (transesterification or reduction) yields enantiomerically enriched products with up to 96 % ee.

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