1174133-84-6Relevant articles and documents
Simple and efficient asymmetric α-alkylation and α,α- bisalkylation of acyclic ketones by using chiral N-amino cyclic carbamate hydrazones
Lim, Daniel,Coltart, Don M.
, p. 5207 - 5210 (2008)
(Chemical Equation Presented) Distinguishing left from right: In the title reactions, chiral N-amino cyclic carbamates (ACCs) substantially diminish the drawbacks associated with the use of chiral dialkyl hydrazines, yet provide excellent stereoselectivity and high yields. In addition, ACCs exhibit a unique directing effect that overrides the inherent selectivity of lithium diisopropylamide (LDA) and enables the asymmetric α,α-bisalkylation of ketones (see scheme).
Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones
Huynh, Uyen,McDonald, Stacey L.,Lim, Daniel,Uddin, Md. Nasir,Wengryniuk, Sarah E.,Dey, Sumit,Coltart, Don M.
, p. 12951 - 12964 (2018/11/30)
The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.
On the regioselectivity and diastereoselectivity of ACC hydrazone alkylation
Huynh, Uyen,Uddin, Md. Nasir,Wengryniuk, Sarah E.,McDonald, Stacey L.,Coltart, Don M.
, p. 432 - 436 (2017/01/13)
The asymmetric α-allylation of 3-pentanone using several different N-amino cyclic carbamate (ACC) auxiliaries is described. The level of asymmetric induction was found to range from er?=?93:7 to er?=?99:1. The factors that lead to compromised selectivity
A simple and efficient approach to the N-amination of oxazolidinones using monochloroamine
Huynh, Uyen,Uddin, Md. Nasir,Wengryniuk, Sarah E.,McDonald, Stacey L.,Coltart, Don M.
, p. 4799 - 4802 (2016/10/05)
Chiral nonracemic N-amino cyclic carbamates (ACCs) are important auxiliaries for certain asymmetric transformations. In the past they have been synthesized from oxazolidinones using methods that require the preparation and use of non-atom economical aminating agents that can be difficult to prepare, and often strong bases. In what follows we describe a mild and operationally simple method for the direct N-amination of oxazolidinones that use NH2Cl derived from commercial bleach.
