Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
6.1.30.5.2 Variation 2: Zweifel's Stereocontrolled Alkene Synthesis

DOI: 10.1055/sos-SD-006-00740

Abu Ali, H.; Dembitsky, V. M.; Srebnik, M.Science of Synthesis, (20056875.

The Zweifel synthesis in its original form provides a stereospecific synthesis of Z-alkenes[‌63‌] via (β-iodoalkyl)borane intermediates, e.g. 38 and 39, in the synthesis of (Z)-1-cyclohexylhex-1-ene (40) (Scheme 17). A major drawback of this alkene synthesis is that it utilizes only one of the two alkyl groups from the starting dialkylborane. Yields are good, but limited by some competing BC bond cleavage by iodine.

Meeeee 88 Meeeeeeee ee (β-Meeeeeeee)eeeeee Meeeeeeeeeeee ee eee Meeeeee Meeeeeeee ee e M-Meeeee[‌88‌]

Me e eeeeeeeee ee eee Meeeeee eeeeeeeee, eee eeeeeeee ee 8,8-eeeeeeeeeeeeeeee (88, M8=M8=Me; M8=M) eeee 8-eeeeeeee-8-eee eeeeeee eee eeeeeeeeeeee (β-eeeeeeeee)eeeeee 88 (M8=Me), eeeee eee ee eeeeeeeeeee ee eee eeeeeeeee eeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee ee Meeeeeeee Meeeee eee e (β-Meeeeeeee)eeeeee Meeeeeeeeeee[‌88‌]

References


Cookie-Einstellungen