Stereoselective Synthesis of Steroids and Related Compounds, IV. Addition of Cerium Reagents Derived from (Trimethylsilyl)propargyl Bromide to Aldehydes | Zendy

Eckenberg Peter | Zendy; Groth Ulrich | Zendy; Köhler Thomas | Zendy

Premium

Stereoselective Synthesis of Steroids and Related Compounds, IV. Addition of Cerium Reagents Derived from (Trimethylsilyl)propargyl Bromide to Aldehydes

Author(s) -

Eckenberg Peter,

Groth Ulrich,

Köhler Thomas

Publication year - 1994

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.199419940707

Subject(s) - chemistry , reagent , regioselectivity , cerium , bromide , trimethylsilyl , stereoselectivity , propargyl , organic chemistry , selectivity , medicinal chemistry , combinatorial chemistry , catalysis

The addition of (trimethylsilyl)propargylmagnesium bromide ( 9 ) to aldehydes afforded predominantly the allenylic alcohols rac ‐ 10 . The regioselectivity of this addition changes dramatically when organocerium reagents were used for the addition. In this case nearly exclusive formation of the homopropargylic alcohols rac ‐ 8 was observed. Highest selectivity for this process was obtained when cerium(III) isopropoxide ( 13 ) was used as a precursor for the formation of the organocerium reagent.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research