67760-91-2Relevant academic research and scientific papers
Asymmetric synthesis of 2°- and 3°-carbinols via B-methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes
Roman, Jose G.,Soderquist, John A.
, p. 9772 - 9775 (2008/03/27)
(Chemical Equation Presented) Simple Grignard procedures provide methallylboranes 1a and 1b in enantiomerically pure form from air-stable precursors in 98% and 95% yields, respectively. These reagents add smoothly to aldehydes and methyl ketones, respecti
Bidirectional Asymmetric Allylboration. A Convenient Asymmetric Synthesis of C2-Symmetric 3-Methylenepentane-1,5-diols and Rapid Access to C2-Symmetric Spiroketals
Barrett, Anthony G. M.,Braddock, D. Christopher,de Koning, Pieter D.,White, Andrew J. P.,Williams, David J.
, p. 375 - 380 (2007/10/03)
The double allylboration of aldehydes using 1,3-bis(diisopinocampheylboryl)-2-methylenepropanes (R,R)-3 and (S,S)-3 under Brown's salt-free conditions provides C2-symmetric 3-methylenepentane-1,5-diols 1 in excellent enantiomeric excess. The absolute stereochemistry of the products was confirmed by a single-crystal X-ray study of bis-Mosher ester 6g. Desymmetrization and further functionalization of diol 1a were achieved by treatment of the bis-BOC carbonate 13 with IBr in toluene at -80°C to give cyclic iodocarbonate 14 as a single diastereomer. This methodology is also applicable in natural product synthesis; enantiomerically pure spiroketals 1,7-dioxaspiro[5.5]-undecanes 18 and 25, the latter representing an expedient synthesis of the AB ring system of the spongistatins 20, were easily accessed from simple starting materials in excellent yields and selectivities.
ASYMMETRIC METHALLYLBORATION OF PROCHIRAL ALDEHYDES WITH METHALLYLDIISO-PINOCAMPHEYLBORANE. SYNTHESIS OF 2-METHYL-1-ALKEN-1-OLS IN 90percent ENAN-TIOMERIC PURITIES
Brown, Herbert C.,Jadhav, Prabhakar K.,Perumal, P. Thirumalai
, p. 5111 - 5114 (2007/10/02)
Methallyldiisopinocampheylborane, on condensation with aldehydes, provides 2-methyl-1-alken-4-ols in 90percent enantiomeric purities.
Stereoselektive Synthese von Alkoholen, VII. Optisch aktive Homoallylalkohole durch Addition chiraler Boronsaeureester an Aldehyde
Hoffmann, Reinhard W.,Herold, Thomas
, p. 375 - 383 (2007/10/02)
Addition of the chiral boronates 1 and 4 to aldehydes led to homoallyl alcohols 2 and 5 of uniform absolute configuration.On addition to saturated aldehydes an asymmetric induction of around 70percent e. e. could be achieved.
