The stereochemistry of aziridine borane lithiation: diastereoselectivity and enantioselectivity

Vedejs, E.; Prasad, A. S. B.; Kendall, John T.; Russel, Jonathon S.

doi:10.1016/j.tet.2003.09.035

“…When the complexation of aminoaziridines 1 was performed with a commercial BH 3 ⋅THF solution, the same borane complexes 2 were also isolated in high yield (Scheme and Table 1). 3a A similar yield and purity of complexes 2 (Table 1) was obtained with both methodologies and, consequently, the cheaper BF 3 ⋅Et 2 O/LiAlH 4 methodology is a valuable alternative to the use of BH 3 ⋅THF solution.…”

Section: Methodsmentioning

confidence: 62%

Synthesis and Stereoselective Lithiation of Enantiopure 2‐(1‐Aminoalkyl)aziridine–Borane Complexes

Concellón

¹

,

Suárez

²

,

García-Granda

³

et al. 2004

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Two alternative methodologies can be used to obtain enantiopure aziridine–borane complexes 2: successive treatment of 2‐(1‐aminoalkyl)aziridines 1 with BF3⋅Et2O and LiAlH4 or by direct reaction with BH3⋅THF (see scheme, Bn=benzyl). The complexes 2 can be deuterated or silylated highly stereoselectively at C3 by reaction with sBuLi and subsequent treatment with D2O or ClSiMe3, respectively.

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“…134 The direct lithiation of aziridines using secbutyllithium/TMEDA has been facilitated when the next carbon atom is occupied by an oxazolinyl group, which can also affect the stereoselectivity of the further reaction with electrophiles due to their complexating properties. 136 In addition, the formation of an aziridineborane complex facilitates the α-metalation and the control of the stereochemistry, 137 the process being also performed with enantiopure complexes. …”

Section: Scheme 17mentioning

confidence: 99%

Metalated heterocycles in organic synthesis: Recent applications

Chinchílla¹,

Nájera²,

Yus³

2007

Arkivoc

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“…134 The direct lithiation of aziridines using secbutyllithium/TMEDA has been facilitated when the next carbon atom is occupied by an oxazolinyl group, which can also affect the stereoselectivity of the further reaction with electrophiles due to their complexating properties. 136 In addition, the formation of an aziridineborane complex facilitates the α-metalation and the control of the stereochemistry, 137 …”

Section: Scheme 17mentioning

confidence: 99%