SYNTHESIS OF CHIRAL SULFONYLMETHYL ISOCYANIDES, AND COMPARISON OF THEIR PROPENSITIES IN ASYMMETRIC INDUCTION REACTIONS WITH ACETOPHENONES

DOI: 10.1016/S0040-4020(01)87684-5

Source and publish data:

Tetrahedron p. 5073 - 5088 (1987)

Update date:2022-08-04

Topics:

Authors:

Hundscheid, Frans J. A.

Tandon, Vishnu K.

Rouwette, Pieter H. F. M.

Leusen, Albert M. van

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Article abstract of DOI:10.1016/S0040-4020(01)87684-5

Seven chiral analogues of tosylmethyl isocyanide (TosMIC) were synthesized in order to investigate and compare their ability to achieve asymmetric induction in base mediated reactions with acetophenone and trifluoracetophenone.Acid hydrolysis of the intermediate 2-oxazolines (10 and 11) gave optically active α-hydroxy aldehydes (12 and 13).

Full text of DOI:10.1016/S0040-4020(01)87684-5

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