Highly Enantioselective Synthesis of Chiral Allenes by Sequential Creation of Stereogenic Center and Chirality Transfer in a Single Pot Operation

作者：Periasamy Mariappan^*; Sanjeevakumar Nalluri; Dalai Manasi; Gurubrahamam Ramani; Reddy Polirnera Obula

来源：Organic Letters, 2012, 14(12): 2932-2935.

DOI：10.1021/ol300717e

Chiral allenes are readily accessed in a single pot operation in the reaction of terminal alkynes, aldehydes, chiral secondary amines, and zinc halides in good yields (up to 77% yield) and excellent enantioselectivities (up to 99% ee) in toluene at 120 degrees C. The reaction proceeds through initial formation of chiral propargylamine intermediates with creation of a new stereogenic center and subsequent chirality transfer via an intramolecular hydride shift to produce chiral allenes with high enantiomeric purities.

• 出版日期2012-6-15